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WO1998004525A1 - Imides cycliques a cinq membres n-aryle fongicides - Google Patents

Imides cycliques a cinq membres n-aryle fongicides Download PDF

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Publication number
WO1998004525A1
WO1998004525A1 PCT/GB1997/002012 GB9702012W WO9804525A1 WO 1998004525 A1 WO1998004525 A1 WO 1998004525A1 GB 9702012 W GB9702012 W GB 9702012W WO 9804525 A1 WO9804525 A1 WO 9804525A1
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WIPO (PCT)
Prior art keywords
optionally substituted
hydrogen
compounds according
alkyl
compounds
Prior art date
Application number
PCT/GB1997/002012
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English (en)
Inventor
Peter John West
Clive Leonard Cornell
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Agrevo Uk 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 Agrevo Uk Limited filed Critical Agrevo Uk Limited
Priority to AU37002/97A priority Critical patent/AU3700297A/en
Publication of WO1998004525A1 publication Critical patent/WO1998004525A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—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
    • 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/34—Oxygen atoms

Definitions

  • This invention relates to compounds having pesticidal, especially fungicidal, insecticidal and acaricidal, activity.
  • the invention provides compounds of general formula I
  • A is O, S or NR ⁇ ; where R ⁇ is hydrogen, cyano, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl or optionally substituted acyl;
  • R 2 and R 3 which may be the same or different, are hydrogen, cyano, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl or optionally substituted acyl;
  • D is CR R 5 , CR 4 , NR 4 , N, 0 or S; where R 4 and R 5 , which may be the same or different, are hydrogen, cyano, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl or optionally substituted acyl;
  • E is O, S or NR6; where ⁇ is hydrogen, cyano, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl or optionally substituted acyl; provided that when B is NR 2 , then D is CR 4 R 5 , O or S; and when B is N, then where the dotted line signifies that a single or a double bond can be present as appropriate;
  • R9 to R ** 2 which may be the same or different, are hydrogen, halogen, cyano, nitro, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or optionally substituted alkoxy, or any two of R-** 1 to
  • R ⁇ 3 and R ⁇ 4 which may be the same or different, and are hydrogen or optionally substituted alkyl;
  • R 1 5 is hydrogen, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted heterocyclyl, optionally substituted acyl or cyano, or R ⁇ and the carbon to which it is
  • 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, imidazolyl, imidazolinyl, imidazoiidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, pyranyl, pyridyl, piperidinyl, dioxanyl, morpholino, dithianyl, thiomorpholino, pyridazinyl, pyr
  • Alkyl groups are preferably of 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 or alkynyl moiety include, halogen, cyano, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted haloalkyl, hydroxy, nitro, optionally substituted amino, acyl, acyloxy, optionally substituted phenyl, optionally substituted heterocyclyl, optionally substituted phenoxy and optionally substituted heterocyclyloxy.
  • Preferred substituents are halogen.
  • Cycloalkyl or cycloalkenyl groups may also be substituted by alkyl.
  • Amino groups may be substituted for example by one or two optionally substituted alkyl or acyl 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, thiomorpholine, or piperidine.
  • acyl includes the residue of sulfur and phosphorus-containing acids as well as carboxylic acids.
  • fused ring system when present, may be carbocyclic or heterocyclic, containing up to 3 heteroatoms; and include aromatic or non-aromatic 5, 6, or 7 membered rings.
  • Preferred fused ring systems include naphthalene and quinoline.
  • Substituents when present on any heterocyclyl group may for example be halogen, CN, NO2, acyl, O-acyl or a group T, OT or S(0) n T, where n is 0, 1 or 2 and T is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted acyl, optionally substituted phenyl, optionally substituted heterocyclyl or optionally substituted amino or two adjacent groups on the ring together with the atoms to which they are attached form a carbocyclic or heterocyclic ring, which may be similarly substituted.
  • Substituents when present on any phenyl group are preferably as defined above for the substituents on the heterocyclyl group.
  • particularly efficacious group of compounds are those of general formula I where A and E are 0.
  • B is CR 2 R 3 or NR 2 ; and/or D is CR 4 R 5 , NR 4 , 0, or S.
  • R 2 is preferably hydrogen or optionally substituted alkyl; and/or R 3 is preferably hydrogen; and/or R 4 is preferably hydrogen or optionally substituted alkyl; and/or R * -> is preferably hydrogen.
  • R " * -3 is preferably hydrogen or optionally substituted alkyl.
  • R "* ** * is preferably optionally substituted alkyl.
  • L is preferably an optionally substituted phenyl group or the group Si(R 22 >3.
  • L is a substituted phenyl, it is preferably substituted by one or more of the following groups C -I -CQ alkyl, C - ⁇ -CQ haloalkyl, C - ⁇ -CQ alkoxy, C -J -CQ alkylthio, C CQ haloalkoxy, halophenoxy, halogen, C3-C8 cycloalkyl, piperidino or pyrimidinyl.
  • R ⁇ to R ⁇ 2 are each hydrogen or halogen.
  • the invention includes individual isomers as well as mixtures thereof.
  • the compounds of the invention have activity as fungicides, especially against fungal diseases of plants, e.g. mildews and particularly barley powdery mildew (Erysiphe graminis) and vine downy mildew (Plasmopara viticola), rice blast (Pyricularia oryzae), cereal eyespot (Pseudocercosporei/a herpotrichoides) , rice sheath blight (PelHcularia sasakii), grey mould (Botrytis cinerea), damping off
  • rice blast Pyricularia oryzae
  • cereal eyespot Pseudocercosporei/a herpotrichoides
  • rice sheath blight PelHcularia sasakii
  • grey mould Botrytis cinerea
  • fungi against which the compounds may be active include other powdery mildews, other rusts, and general pathogens of Deuteromycete, Ascomycete, Phycomycete and Basidomycete origin.
  • the invention thus also provides a method of combating pests (i.e. fungi, insects, nematodes, acarids and weeds) at a locus infested or liable to be infested therewith, which comprises applying to the locus a compound of formula I.
  • pests i.e. fungi, insects, nematodes, acarids and weeds
  • 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 compound 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 suifonates; petroleum suifonates; alkyl-aryl suifonates such as alkyl-benzene suifonates or lower alky
  • butyl-naphthalene sulfonate salts of sulfonated naphthalene-formaldehyde condensates; salts of sulfonated phenol-formaldehyde condensates; or more complex suifonates such as the amide suifonates, 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 suifonates 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 carboxyiic 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 fiowable 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 0.0001 to 1.0 per cent by weight, especially 0.0001 to 0.01 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 5 to 1000 g per hectare, more preferably from 10 to 500 g 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 0.025 to 5 kg per hectare, preferably from 0.05 to 1 kg per hectare.
  • B in CR 2 R 3 ; D is NR 4 and E is 0; may be prepared in two steps by reacting amines VI with isocyanate VII, where Q is a leaving group, followed by cyclisation.
  • Construction of the group -K-L can be performed using a number of strategies either before or after construction of the 5-membered heterocyclyl group.
  • compounds of formula Ik i.e. compounds of general formula I where K is -CH(R ⁇ 3 )-, can be prepared by reacting hydroxy compound IX, which is preferably a phenolic compound, with potassium re -butoxide followed by addition of VII.
  • the title compound was prepared in analogous fashion to Example 1 replacing the 3-trifluoromethylphenylacetyl oxime with o-cresol in stage a). The title compound was obtained as a solid, m.p. 94-5 °C.
  • the title compound was prepared in known manner from o-aminobenzyl alcohol and te/ ⁇ -butyldimethylsiiyl chloride
  • the title compound was prepared in analogous fashion to Example 2 using ⁇ -(o- tolyloxy)-o-toluidine instead of ferf-butyldimethylsilyloxy)-o-toluidine.
  • the product was obtained as a 55:45 mixture of rotamers, ⁇ H N.M.R. ⁇ (ppm) 1 .26 and 1 .50 (3H, d, -CH-Me); 2.20(3H, s, Ph e); 4.10 and 4.20 (1 H, q, -CHMe); 4.90-5.10 (2H, m, -0-CH 2 Ph); and 6.80-7.65 (8H, m, Ar-H).
  • the title compound was prepared in analogous fashion to Example 2 using ethyl isocyanatoethanoate instead of ethyl 2-isocyanatopropionate and the product from Example 1 , stage c), instead of ⁇ -(ferf-butyldimethylsilyloxy)-o-toluidine.
  • the product was obtained as a mixture of rotamers, 1 H N.M.R.
  • the title compound was prepared in similar fashion to Example 1 using ethyl 2- mercaptopropionate instead of N-methylhydroxylamine hydrochloride.
  • Example 3 The title compound was prepared in similar fashion to Example 1 using ethyl mercaptoethanoate instead of ethyl 2-mercaptopropionate.
  • Example 3 Example 3
  • Erysiphe graminis f. sp. hordei barley powdery mildew Erysiphe graminis f. sp. tritici: wheat powdery mildew Pyricularia oryzae: rice blast PelHcularia sasakii: rice sheath blight 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 50% control of the disease at a concentration of 500 ppm (w/v) or less.
  • Compounds 1 and 6 showed activity against Plasmopara viticola; Compounds 4 and 7 showed activity against Pyricularia oryzae; Compound 1 showed activity against PelHcularia sasakii; Compounds 4 and 3 showed activity against Botrytis cinerea; Compound 4 showed activity against Venturia inaequalis; Compounds 1 and 5 showed activity against Erysiphe graminis f. sp. tritici

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

Abstract

Composés définis par la formule générale (I) dans laquelle A est O, S ou NR1; B est CR?2R3, CR2, NR2¿ ou N; D est CR?4R5, CR4, NR4¿, N, O ou S; E est O, S ou NR6; à condition que lorsque B est NR2 alors D est CR4R5, O ou S, et lorsque B est N alors D est CR4; dans laquelle la ligne pointillée signifie qu'une simple ou une double liaison peut être présente selon la nécessité; K est -O-, -S(O)¿n?-, -CHR?13-, -CHR13CHR14¿-, -CR¿13=CR?14-, -C=C-, -CHR13O-, -OCHR?13-, -CHR13S(O)¿n-, -S(O)nCHR13-, -CH(R13)O-N=C(R15)-, -C(R15)=N-OCH(R?13-, -C(R15¿)=N-O-, -O-N=C(R15)-, -CHR15OC(=O)N(R?20),-CH(R13)N(R21)N=C(R15¿)- ou une liaison directe; dans laquelle la fraction représentée à droite de la liaison est attachée à L; L est alkyle éventuellement substitué; alkényle éeventuellement substitué; alkynyle éventuellement substitué, cycloalkyle éventuellement substitué, cycloalkényle éventuellement substitué; hétérocyclyle éeventuellement substitué; phényle éventuellement substitué; ou Si(R22)3; ou R9, K et L avec le cycle phényle M, peuvent former ensemble un système de combinaison cyclique éventuellement substitué. Ces composés présentent une activité pesticide, en particulier fongicide, insecticide et acaricide.
PCT/GB1997/002012 1996-07-27 1997-07-28 Imides cycliques a cinq membres n-aryle fongicides WO1998004525A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU37002/97A AU3700297A (en) 1996-07-27 1997-07-28 Fungicidal n-aryl five-membered cyclic imides

Applications Claiming Priority (2)

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GB9615831.6 1996-07-27
GBGB9615831.6A GB9615831D0 (en) 1996-07-27 1996-07-27 Fungicides

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999020615A3 (fr) * 1997-10-16 1999-06-24 Basf Ag Carbamates de phenyle pesticides substitues, procedes et produits intermediaires permettant de les preparer et leur utilisation
US7763609B2 (en) 2003-12-15 2010-07-27 Schering Corporation Heterocyclic aspartyl protease inhibitors
US7973067B2 (en) 2003-12-15 2011-07-05 Schering Corporation Heterocyclic aspartyl protease inhibitors
US8093254B2 (en) 2006-12-12 2012-01-10 Schering Corporation Aspartyl protease inhibitors
US8178513B2 (en) 2003-12-15 2012-05-15 Schering Corporation Heterocyclic aspartyl protease inhibitors

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