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WO1996016954A1 - Derives de l'acide anthranilique utiles en tant que fongicides - Google Patents

Derives de l'acide anthranilique utiles en tant que fongicides Download PDF

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Publication number
WO1996016954A1
WO1996016954A1 PCT/EP1995/004800 EP9504800W WO9616954A1 WO 1996016954 A1 WO1996016954 A1 WO 1996016954A1 EP 9504800 W EP9504800 W EP 9504800W WO 9616954 A1 WO9616954 A1 WO 9616954A1
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WIPO (PCT)
Prior art keywords
optionally substituted
heterocyclyl
alkyl
cycloalkenyl
alkenyl
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Legal status (The legal status 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 status listed.)
Ceased
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PCT/EP1995/004800
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English (en)
Inventor
Peter Dominic Riordan
Peter John West
Ian Kenneth Boddy
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience Ltd Great Britain
Original Assignee
Agrevo UK Ltd
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Publication date
Application filed by Agrevo UK Ltd filed Critical Agrevo UK Ltd
Priority to EP95941681A priority Critical patent/EP0794950A1/fr
Priority to AU43028/96A priority patent/AU4302896A/en
Publication of WO1996016954A1 publication Critical patent/WO1996016954A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C07D231/38—Nitrogen atoms
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    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • 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
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    • A01N43/80—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 1,2
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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 with nitro or nitroso radicals directly attached to ring carbon atoms
    • C07D333/44—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 with nitro or nitroso radicals directly attached to ring carbon atoms attached in position 5
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    • C07—ORGANIC CHEMISTRY
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
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    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Definitions

  • This invention relates to new derivatives of anthranilic acid useful as fungicides.
  • A is a 5 membered optionally substituted, heteroaryl group comprising at least one hetero atom selected from nitrogen, sulfur and oxygen, which is optionally substituted by one or more of the group R 2 ;
  • R 1 is alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, or amino, (each of which is optionally substituted), Y 1 -X- f halogen, cyano, nitro, acyl, optionally substituted heterocyclyl or optionally substituted phenyl; or two adjacent groups together with the carbon atoms to which they are attached can form an optionally substituted benzo ring;
  • R 2 has the same meaning as R 1 or two adjacent groups together with the carbon atoms to which they are attached can form an optionally substituted heterocyclic ring;
  • Y is alkyl, cycloalkyl, cycloalkenyl, alkenyl or alkynyl, each of which is optionally substituted, hydrogen or acyl;
  • Y 1 has the same meaning as Y or is optionally substituted phenyl or optionally substituted heterocyclyl;
  • R 3 is alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, phenyl or heterocyclyl, each of which is optionally substituted, hydrogen or an inorganic or organic cationic group;
  • X 1 and X 2 which may be the same or different, are 0 or S;
  • R 5 , R ⁇ and R 7 which may be the same or different, are alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, phenyl or heterocyclyl, each of which is optionally substituted or hydrogen or R 6 and R 7 together with the atom(s) to which they are attached can form a ring; and n is 0 to 4, together with complexes with metal salts, as well as salts with bases of compounds which are acids and salts with acids of compounds which are bases, with the proviso that when Z is methoxycarbonyl and Y is hydrogen and ring A is furyl or thienyl, then either n is not 0 or ring A is substituted.
  • rings that A can be include, thiophene, furan, pyrrole, pyrazole, imidazole, thiazole, isothiazole, oxazole, isoxazole, thiadiazole, oxadiazole and triazole.
  • the ring comprises a sulfur atom this may be in an oxidised state either as sulfoxide or sulfone.
  • Alkyl groups are preferably of 1 to 20, eg 1 to 6, carbon atoms.
  • Alkenyl and alkynyl groups are generally of 3 to 6 carbon atoms.
  • Cycloalkyl or cycloalkenyl groups are preferably of 3 to 8 carbon atoms.
  • Substituents when present on any alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, alkoxy or alkylthio group, include halogen, cyano, alkoxy (e.g. of 1 to 4 carbon atoms, and which may be substituted, e.g. by halo), hydroxy, alkylthio, nitro, optionally substituted amino, carboxy, alkoxycarbonyl, acyl, acyloxy, heterocyclyl and aryl.
  • Cycloalkyl or cycloalkenyl groups may also be substituted by alkyl.
  • Aryl groups are usually phenyl, optionally substituted, e.g. by one or more of the same groups as defined for R 1 .
  • heterocyclyl includes both aromatic and non-aromatic heterocyclyl groups.
  • Heterocyclyl groups are generally 5, 6 or 7-membered rings containing up to 4 hetero atoms selected from nitrogen, oxygen and sulfur.
  • Examples of heterocyclyl groups are furyl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, dioxolanyl, oxazolyl, thiazolyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, pyranyl, pyridyl, piperidinyl, dioxanyl, morpholino, dithianyl, thiomorpholino, pyridazinyl, pyrimidinyl, pyrazinyl, piperazin
  • Amino groups may be substituted for example by one or two optionally substituted alkyl, acyl or sulfonyi groups, or two substituents can form a ring, preferably a 5 to 7-membered ring, which may be substituted and may contain other hetero atoms, for example morpholine, thiomorphoiine, or piperidine.
  • acyl includes the residue of sulfur and phosphorus-containing acids as well as carboxylic acids.
  • Complexes of compounds of the invention are usually formed from a salt of formula An 2 , in which is a divalent metal cation, e.g. copper, manganese, cobalt, nickel, iron or zinc and An is an anion, e.g. chloride, nitrate or sulfate.
  • the compounds of the invention have activity against a wide range of pathogens of Deuteromycete, Ascomycete, Phycomycete and Basidiomycete origin, and especially against fungal diseases of plants, e.g.
  • the compounds of the invention are generally formulated in conventional compositions used for fungicides. These compositions can contain one or more additional pesticides, for example compounds known to possess herbicidal, fungicidal, insecticidal, acancidal or nematicidal properties.
  • 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 taunne 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 taunne 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, naphthe ⁇ ate 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.
  • the composition comprises a compound of the invention dispersed in a liquid medium, preferably water. It is often convenient to supply the consumer with a primary composition which can be diluted with water to form a dispersion having the desired concentration.
  • the primary composition can be provided in any one of the following forms. It can be a dispersible solution which comprises a compound of the invention dissolved in a water-miscible solvent with the addition of a dispersing agent.
  • a further alternative comprises a compound of the invention in the form of a finely ground powder in association with a dispersing agent and intimately mixed with water to give a paste or cream which can if desired be added to an emulsion of oil in water to give a dispersion of active ingredient in an aqueous oil emulsion.
  • An emulsifiable concentrate comprises a compound of the invention dissolved in a water-immiscible solvent together with an emulsifying agent and which is formed into an emulsion on mixing with water.
  • a dusting powder comprises a compound of the invention intimately mixed 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 adsorbed or absorbed on a pre-granular diluent, for example. Fuller's earth, attapulgite or limestone grit.
  • a wettable powder usually comprises the active ingredient in admixture with a suitable surfactant and an inert powder diluent such as china clay.
  • Another suitable concentrate particularly when the product is a solid, is a flowable suspension concentrate which is formed by grinding the compound with water, a wetting agent and a suspending agent.
  • the concentration of the active ingredient in the composition of the present invention is preferably within the range of 1 to 30 per cent by weight, especially 5 to 30 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 compounds of the invention may be prepared in known manner, for example by reacting a compound of formula II
  • the compounds of formula II and III are either known or can be prepared in known manner.
  • A is a sulfur containing ring
  • the sulfur can be oxidised in known manner.
  • Example 2 A solution of methyl anthranilate (4.3 g) and triethylamine (3.93 ml) in tetrahydrofuran was added dropwise with ice-bath cooling and stirring to a solution of 5-nitro-2-furancarbonyl chloride (5 g) in tetrahydrofuran. The mixture was stirred for 5 hours, and evaporated under reduced pressure. The residue was washed with water, dissolved in dichloromethane and the organic extract washed with aqueous sodium hydrogen carbonate and brine, dried and evaporated. The residue was washed with light petroleum to give methyl N-(5-nitro-2-furan- carbonyDanthranilate, m.p. 1 79-81 ° . (compound 2)
  • Example 4 A stirred mixture of 4-methoxy-5-methoxycarbonyl-2-thiophenecarboxylic acid (1 g) and thionyl chloride (5 ml) was heated under reflux for 9 minutes. The mixture was cooled, evaporated and the residue (comprising crude 4-methoxy- 5-ethoxycarbonyl-2-furancarbonyl chloride) was treated with methyl anthranilate and triethylamine in a similar manner to Example 1 . The reaction mixture was poured into water and the precipitate collected, washed with water and dried to give methyl N-(4-methoxy-5-methoxycarbonyl-2-thiophenecarbonyl)anthranilate, m.p. 1 76-9°. (compound 4)
  • Example 5 A mixture of 2-methoxy-1 -methyl-5-imidazolecarboxylic acid (1 g) and 2-chloro-
  • Phytophthora infestans late tomato blight
  • P/asmopara viticola vine downy mildew
  • Erysiphe graminis barley powdery mildew
  • Pyricularia oryzae rice blast Pellicularia sasakii: rice sheath blight (PS)
  • Botrytis cinerea grey mould Venturia inaequalis: apple scab
  • Leptosphaeria nodorum glume blotch
  • Aqueous solutions or dispersions of the compounds at the desired concentration, including a wetting agent, were applied by spray or by drenching the stem base of the test plants, as appropriate. Plants or plant parts were then inoculated with appropriate test pathogens and 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 affected part of the plant was visually estimated. Compounds were considered active if they gave greater than

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

Abstract

Composés de la formule (I) dans laquelle A représente un groupe hétéroaryle à 5 chaînons, éventuellement substitué, comprenant au moins un hétéroatome choisi parmi azote, soufre et oxygène, lequel est éventuellement substitué par un ou plusieurs substituants du groupe R2; R1 représente alkyle, cycloalkyle, cycloalcényle, alcényle, alcynyle ou amino (chacun de ceux-ci étant éventuellement substitué), Y1-X-, halogène, cyano, nitro, acyle, acyloxy, hétérocyclyle éventuellement substitué ou phényle éventuellement substitué; ou il représente deux groupes adjacents qui, avec les atomes de carbone auxquels ils sont attachés, peuvent former un noyau benzo éventuellement substitué; R2 possède les mêmes notations que R1, ou il représente deux groupes adjacents qui, avec les atomes de carbone auxquels ils sont attachés, peuvent former un noyau hétérocyclique éventuellement substitué; Y représente alkyle, cycloalkyle, cycloalcényle, alcényle ou alcynyle, chacun étant éventuellement substitué, hydrogène ou acyle; Y1 possède la même notation que Y ou il représente phényle éventuellement substitué ou hétérocyclyle éventuellement substitué; Z représente C(=X?1)-X2-R3¿, cyano, nitro, amino, acyle, hétérocyclyle éventuellement substitué, -C(R?5)=N-OR6¿ ou -C(R?5)=N-NR6R7; R3¿ représente alkyle, cycloalkyle, cycloalcényle, alcényle, alcynyle, phényle ou hétérocyclyle, chacun étant éventuellement substitué, hydrogène ou un groupe cationique inorganique ou organique; X1 et X2 qui peuvent être semblables ou différents, représentent O ou S; R?5, R6 et R7¿, qui peuvent être semblables ou différents, représentent alkyle, cycloalkyle, cycloalcényle, alcényle, alcynyle, phényle ou hétérocyclyle, chacun étant éventuellement substitué, ou hydrogène, ou bien R6 et R7, ensemble avec l'atome (les atomes) auquel (auxquels) ils sont attachés, peuvent former un noyau; et n vaut 0 à 4. Ces composés possèdent une activité fongicide.
PCT/EP1995/004800 1994-12-02 1995-12-01 Derives de l'acide anthranilique utiles en tant que fongicides Ceased WO1996016954A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP95941681A EP0794950A1 (fr) 1994-12-02 1995-12-01 Derives de l'acide anthranilique utiles en tant que fongicides
AU43028/96A AU4302896A (en) 1994-12-02 1995-12-01 Derivatives of anthranilic acid useful as fungicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9424379A GB9424379D0 (en) 1994-12-02 1994-12-02 Fungicides
GB9424379.7 1994-12-02

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WO1996016954A1 true WO1996016954A1 (fr) 1996-06-06

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EP (1) EP0794950A1 (fr)
AU (1) AU4302896A (fr)
GB (1) GB9424379D0 (fr)
IL (1) IL116234A0 (fr)
WO (1) WO1996016954A1 (fr)
ZA (1) ZA9510223B (fr)

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WO1997030047A1 (fr) * 1996-02-17 1997-08-21 Agrevo Uk Limited 1,2,4 oxadiazoles fongicides et analogues
WO1998018792A1 (fr) * 1996-10-28 1998-05-07 Merck Sharp & Dohme Limited DERIVES DE LA THIENYLCYCLOHEXANONE UTILISES COMME LIGANDS DU SOUS-TYPE α-5 DE RECEPTEUR DU GABA¿A?
GB2336588A (en) * 1998-04-23 1999-10-27 Merck Sharp & Dohme Benzo[c]thiophene Derivatives for Enhancing Cognition
US6143773A (en) * 1998-04-23 2000-11-07 Merck Sharp & Dohme Limited Substituted thienobenzisoxazole derivatives for enhancing cognition
US6156761A (en) * 1998-04-23 2000-12-05 Merck Sharpe & Dohme Limited Substituted tetralone derivatives for enhancing cognition
WO2001058879A1 (fr) * 2000-02-09 2001-08-16 The Procter & Gamble Company 2-phenylcarbamoyl-benzimidazoles
US6395766B1 (en) 1998-06-04 2002-05-28 Merck Sharp & Dohme Limited Tetrahydroindolone derivatives as gabaaalpha5 ligands for enhancing cognition
JP2002524557A (ja) * 1998-09-16 2002-08-06 バイエル アクチェンゲゼルシャフト イソチアゾールカルボン酸アミド類
WO2003016304A1 (fr) * 2001-08-15 2003-02-27 E. I. Du Pont De Nemours And Company Amides aryle ortho-heterocycliques substitues permettant de lutter contre des ravageurs invertebres
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WO2004018461A3 (fr) * 2002-08-23 2004-08-26 Upjohn Co Derives d'acide benzoique antibacteriens
WO2005004606A3 (fr) * 2003-07-10 2005-04-21 Bayer Cropscience Ag Pyridinylanilides
WO2005085234A3 (fr) * 2004-03-03 2006-01-26 Syngenta Participations Ag Nouveaux insecticides
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WO2009054468A1 (fr) * 2007-10-24 2009-04-30 Astellas Pharma Inc. Composé à base d'azolecarboxamide ou son sel
JP2009535311A (ja) * 2006-04-28 2009-10-01 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 殺虫化合物
WO2010035886A1 (fr) * 2008-09-25 2010-04-01 住友化学株式会社 Composition à usage agricole qui contrôle ou empêche une maladie botanique provoquée par des agents pathogènes de plante
EP1846388A4 (fr) * 2005-01-25 2011-12-07 Synta Pharmaceuticals Corp Composes de thiophene utilises contre l'inflammation et les troubles lies a l'immunite
US8163746B2 (en) 2006-04-19 2012-04-24 Astellas Pharma Inc. Azolecarboxamide derivative
CN104529900A (zh) * 2014-12-31 2015-04-22 南开大学 1-取代-n-取代苯基-5-氨基-1h-吡唑-4-甲酰胺类化合物的杀菌活性
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