WO1996029301A1 - Composes fongicides - Google Patents

Composes fongicides Download PDF

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Publication number
WO1996029301A1
WO1996029301A1 PCT/GB1996/000658 GB9600658W WO9629301A1 WO 1996029301 A1 WO1996029301 A1 WO 1996029301A1 GB 9600658 W GB9600658 W GB 9600658W WO 9629301 A1 WO9629301 A1 WO 9629301A1
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WIPO (PCT)
Prior art keywords
optionally substituted
compound
compound according
compounds
methyl
Prior art date
Application number
PCT/GB1996/000658
Other languages
English (en)
Inventor
Clive Leonard Cornell
Ian Christopher Richards
Geoffrey Gower Briggs
Jean-Louis Brayer
Jean-Pierre Demoute
Original Assignee
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 AU51160/96A priority Critical patent/AU5116096A/en
Priority to EP96907584A priority patent/EP0819111A1/fr
Priority to JP8528193A priority patent/JPH11503114A/ja
Publication of WO1996029301A1 publication Critical patent/WO1996029301A1/fr

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    • 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
    • A01N43/02—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
    • A01N43/24—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 two or more hetero atoms
    • A01N43/26—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 two or more hetero atoms five-membered rings
    • A01N43/28—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • 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
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only 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
    • 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
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N43/80—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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers

Definitions

  • This invention relates to compounds having pesticidal, especially fu ⁇ gicidal, insecticidal and acaricidal, activity.
  • X and Y which are the same or different, are hydrogen, halogen, optionally substituted alk ⁇ l, optionally substituted cycloalkyl, optionally substituted cycloalkylalk ⁇ l, optionally substituted alkenyi, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted ar ⁇ lalkoxy, optionally substituted heteroarylalkoxy, optionally substituted acyioxy, optionally substituted amino, acylamino, nitro cyano, -C0 2 R 3 , -CONR 4 R 5 , or -COR ⁇ , except that X and Y are not both hydrogen;
  • R 1 and R 2 which are the same or different, are alkyl or fluoroalkyl; and R 3 , R 4 , R 5 and R ⁇ , which are the same or different, are hydrogen, alkyl, alkenyi, alkynyl, optionally substituted aryl, optionally substituted aralkyl, or cycloalkylalkyl.
  • the invention provides compounds of formula I
  • R is alkyl, cycloalkyl, alkenyi, cycloalkenyl, alkynyl, phenyl or heterocyclyl, each of which is optionally substituted, or is hydrogen, and acid addition salts of any compounds which are basic and basic addition salts of any compounds which are acidic.
  • the R-O- group is preferably attached to the naphthyl at the 6 or 7 position and more preferably at the 7-position.
  • Substituents when present on any phenyl or heterocyclyl group include for example halogen, cyano or nitro, or the group D-(L) m -, where m is 0 or 1 , L is 0, S, SO,.S0 2 , CO, O-CO or CO-O, and D is has the same meaning as R (except hydrogen when m is 0) or is optionally substituted amino; or two adjacent groups on the ring together with the atoms to which they are attached can form an carbocyciic or heterocyclic ring which may be similarly substituted as for phenyl.
  • 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, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazol ⁇ l, thiadiazolyl, pyranyl, pyridyl, piperidinyl, dioxanyl, morpholino, pyridazinyl, pyrimidinyl, pyrazinyl,
  • Alkyl groups are preferably of 1 to 8, e.g. 1 to 6, carbon atoms.
  • Alkenyi 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, alkenyi or alkynyl moiety include halogen, cyano, optionally substituted alkoxy, optionally substituted alkylthio, hydroxy, nitro, optionally substituted amino, acyl, acyloxy, optionally substituted phenyl, optionally substituted heterocyclyl, optionally substituted phenoxy and optionally substituted heterocyclyloxy.
  • 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.
  • the compounds of the invention exist as the E and Z isomers and the invention includes individual isomers as well as mixtures of these, with the E-isomer being preferred.
  • a preferred group of compounds are those where R is alkyl, substituted by one or more alkoxy, aryloxy, heteroaryloxy or heterocyclyoxy groups, (all of which may be optionally substituted).
  • R is alkyl, substituted by one or more alkoxy, aryloxy, heteroaryloxy or heterocyclyoxy groups, (all of which may be optionally substituted).
  • Another preferred group of compounds are those where R is optionally substituted heteroaryl, e.g. pyrimidinyl, 1 ,2,4-thiadiazolyl, quinazolinyl or pyridyl.
  • a particularly preferred group of compounds are those where R is an optionally substituted C C ⁇ linear or branched chain alkyl group, preferably substituted by one or more halogen atoms, especially fluorine and/or chlorine and/or bromineatoms.
  • R is an optionally substituted C C ⁇ linear or branched chain alkyl group, preferably substituted by one or more halogen atoms, especially fluorine and/or chlorine and/or bromineatoms.
  • halogen atoms especially fluorine and/or chlorine and/or bromineatoms.
  • examples of such preferred groups include CF 2 H, CF 2 Br, CF 2 CF 2 CI, CFCICF 2 CI. CF 2 CF 2 H or CF 2 CHCI 2 .
  • the invention includes any compound of formula I and specifically listed.
  • the compounds of the invention have activity as fungicides, especially against fungal diseases of plants, e.g. mildews and particularly barley powdery mildew iErysiphe graminis) and vine downy mildew iPlasmopara viticola), rice blast iPyric ⁇ laria oryzae), cereal eyespot (Pseudocercosporella herpotrichoides) , rice sheath blight iPellicularia sasakii), grey mould iBotrytis cinerea), damping off iPxhizoctonia solani), wheat brown rust iPuccinia recondita), late tomato or potato blight iPhytophthora infestans), apple scab i Vent ⁇ ria inaequalis), glume blotch (Leptosphaeria nodorum).
  • Other fungi against which the compounds may be active include other powdery mildews, other rusts, and general
  • the compounds of the invention also have insecticidal, acaricidal and nematicidal activity and are particularly useful in combating a variety of economically important insects, acarids and plant nematodes, including animal ectoparasites and especially Diptera, such as sheep blow-fly, Lucilia sericata, and house-flies, Musca domestica; Lepidoptera, including Plutella xylostella, Spodoptera littoralis, Heliothis armigera and Pieris brassicae; Homoptera, including aphids such as Megoura viciae and Aphis craccivora; Coleoptera, including corn rootworms iDiabrotica spp., e.g.
  • 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 octadec ⁇ i suifate or sodium cetyl suifate; ethox ⁇ lated fatty alcohol sulfates; ethoxylated alkyiphenol sulfates; lignin sulfonates; petroleum sulfonates; alkyl-aryl sulfonates such as alkyl-benzene sulf
  • butyl-naphthalene sulfonate salts of sulfonated naphthalene-formaldehyde condensates; salts of sulfonated phenol-formaldehyde condensates; or more complex sulfonates such as the amide sulfonates, e.g. the sulfonated condensation product of oleic acid and N-methyl taurine or the dialkyl sulfosuccinates, e.g. the sodium sulfonate of dioctyl succinate.
  • amide sulfonates e.g. the sulfonated condensation product of oleic acid and N-methyl taurine or the dialkyl sulfosuccinates, e.g. the sodium sulfonate of dioctyl succinate.
  • Nonionic agents include condensation products of fatty acid esters, fatty alcohols, fatty acid amides or fatty-alkyl- or alkenyl-substituted phenols with ethylene oxide, fatty esters of polyhydric alcohol ethers, e.g. sorbitan fatty acid esters, condensation products of such esters with ethylene oxide, e.g. polyoxyethylene sorbitan fatty acid esters, block copolymers of ethylene oxide and propylene oxide, acetylenic glycols such as 2,4,7,9-tetramethyl-5-decyne-4,7-diol, or ethoxylated acetylenic glycols.
  • a cationic surface-active agent examples include, for instance, an aliphatic mono-, di-, or polyamine as an acetate, naphthenate or oleate; an oxygen-containing amine such as an amine oxide or polyoxyethylene alkylamine; an amide-linked amine prepared by the condensation of a carboxylic acid with a di- or polyamine; or a quaternary ammonium salt.
  • compositions of the invention can take any form known in the art for the formulation of agrochemicals, for example, a solution, a dispersion, an aqueous emulsion, a dusting powder, a seed dressing, a fumigant, a smoke, a dispersible powder, an emulsifiable concentrate or granules. Moreover it can be in a suitable form for direct application or as a concentrate or primary composition which requires dilution with a suitable quantity of water or other diluent before application.
  • An emulsifiable concentrate comprises a compound of the invention dissolved in a water-immiscible solvent which is formed into an emulsion with water in the presence of an emulsifying agent.
  • a dusting powder comprises a compound of the invention intimately mixed and ground with a solid pulverulent diluent, for example, kaolin.
  • a granular solid comprises a compound of the invention associated with similar diluents to those which may be employed in dusting powders, but the mixture is granulated by known methods. Alternatively it comprises the active ingredient absorbed or adsorbed on a pre-granular diluent, for example. Fuller's earth, attapulgite or limestone grit. Wettable powders, granules or grains usually comprise the active ingredient in admixture with a suitable surfactant and an inert powder diluent such as china clay.
  • Another suitable concentrate is a flowable suspension concentrate which is formed by grinding the compound with water or other liquid, a wetting agent and a suspending agent.
  • the concentration of the active ingredient in the composition of the present invention, as applied to plants is preferably within the range of 0.0001 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 1 0 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.
  • it is practicable to treat the roots of a plant before or during planting for example, by dipping the roots in a suitable liquid or solid composition.
  • a suitable rate of application is from 0.001 to 1 kg per hectare, preferably from
  • the compounds of the invention may be prepared, in known manner, in a variety of ways, for example
  • Q is a leaving group, preferably halogen and especially bromine, with a compound of formula III
  • reaction is carried out under basic conditions e.g. in the presence an alkali metal carbonate or hydroxide, and also in the presence of a metal salt catalyst, such as cuprous iodide.
  • a metal salt catalyst such as cuprous iodide.
  • the compounds of formula II are known, e.g. EP 538097, or can be prepared in known manner.
  • a phosphorus ylide derived from e.g. a phosphonium salt of formula
  • the compound of formula IX can be obtained by reducing the compounds of formula IV, in a Wolff-Kischner reduction, e.g. by using hydrazine in the presence of a base e.g. an alkali metal alkoxide. d) by reacting a compound of formula X
  • Acetylenic compounds (XIII) are described in EP 566,455 (Roussel Uclaf) and may be converted to compounds (X) according to the following scheme.
  • Halo compounds (XVI) are described in EP 566,455 (Roussel Uclaf) and may be converted to compounds (X) according to the following scheme.
  • Potassium tert.-butoxide (1 .0 g) was added to a suspension of methoxymethyl- triphenylphosphonium chloride (3.34 g) in dry ether (25 ml) under nitrogen. The mixture stirred for 30 minutes at room temperature. The supernatant liquid was decanted into a dropping funnel and added over 5 minutes, with stirring, to a solution of methyl 2-[7-(4,6-dimethoxypyrimidin-2-yloxy)-1 -naphthyl]-2-oxoacetate (1 .63 g) in dry tetrahydrofuran (25 ml).
  • Methyl (E and Z)-2-f7-hvdroxy-1 -naphthyll-3-methoxyacrylate 49.5 g (0.144 mol) (methoxymethyl)triphenylphosphonium chloride was suspended in 400 ml dry ether. The reaction mixture was cooled to 0°, 57.6 ml (0.144 mol) n-butyllithium (2.5 m in hexane) was the added with syringe over a period of 5 minutes. The bright red suspension was allowed to come to room temperature and then stirred for 30 minutes. The formed solid was allowed to settle. The solution was transferred into another flask using a cannula. The residue was washed with 100 mi dry ether.
  • Methyl (E)-2-[7-acetyl-1 -naphthyll-3-methoxyacrylate ( 1 .0 g) was dissolved in dry ether ( 10 ml) and dry dichloromethane ( 10 ml) and cooled to -78 ° under an atmosphere of nitrogen.
  • Methyl magnesium bromide (2.4 ml of a 3M solution in ether) was added directly and the reaction mixture stirred for 2 hours at -78 ° before warming to room temperature and then pouring onto water (100 ml) and dichloromethane (100 ml). Isolation gave the product as a yellow solid, which was used without further purification.
  • reaction mixture was carefully poured onto ice-water and acidified with hydrochloric acid.
  • Compounds are assessed for activity against one or more of the following:
  • Phytophthora infestans late tomato blight (PI)
  • Plasmopara viticola vine downy mildew (PV)
  • Pellicula a sasakii rice sheath blight (PS)
  • Botrytis cinerea grey mould (BC)
  • Venturia inaequalis apple scab (VI)
  • Leptosphaeria nodorum glume blotch (LN)
  • 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
  • Bean plants are treated by dipping the leaves in an aqueous acetone solution of active ingredient (50% acetone, 50% water) then dried under a ventilated hood. The leaves are then infested with 20 adult Aphis craccivora females per leaf and kept at 22° under a intense light conditions. Mortality checks are carried out after 48 hours. Compounds were considered active if they gave greater than 75% mortality of the insects at a concentration of 300 ppm(W/v) or less. Activities are shown in the following table
  • Haricot bean plants comprising 2 leaves infested with 30 Tetranychus urticae females per leaf and put under a ventilated hood under a luminous ceiling with constant illumination.
  • the plants are treated with a 4 ml of an aqueous acetone solution of active ingredient per plant.
  • the leaves are left to dry for 30 minutes.
  • Mortality checks are carried out after 72 hours. Compounds were considered active if they gave greater than 75% mortality of the insects at a concentration of 300 ppm(W/v) or less. Activities are shown in the following table

Landscapes

  • 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)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Composés de la formule (I) dans laquelle R représente alkyle, cycloalkyle, alcényle, cycloalcényle, alkynyle, phényle ou hétérocyclyle, chacun pouvant être substitué facultativement, ou représente hydrogène. Ces composés ont une activité pesticide, notamment une activité fongicide.
PCT/GB1996/000658 1995-03-21 1996-03-19 Composes fongicides WO1996029301A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU51160/96A AU5116096A (en) 1995-03-21 1996-03-19 Fungicidal compounds
EP96907584A EP0819111A1 (fr) 1995-03-21 1996-03-19 Composes fongicides
JP8528193A JPH11503114A (ja) 1995-03-21 1996-03-19 殺菌性化合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9505651.1A GB9505651D0 (en) 1995-03-21 1995-03-21 AgrEvo UK Limited
GB9505651.1 1995-03-21

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WO1996029301A1 true WO1996029301A1 (fr) 1996-09-26

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EP (1) EP0819111A1 (fr)
JP (1) JPH11503114A (fr)
AU (1) AU5116096A (fr)
GB (1) GB9505651D0 (fr)
IL (1) IL117595A0 (fr)
WO (1) WO1996029301A1 (fr)
ZA (1) ZA962319B (fr)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998005652A2 (fr) * 1996-08-01 1998-02-12 E.I. Du Pont De Nemours And Company Amides cycliques arthropodicides et fongicides
WO2000047212A1 (fr) * 1999-02-10 2000-08-17 Astrazeneca Ab Derives de quinazoline utilises comme inhibiteurs de l'angiogenese
US7268230B2 (en) 2002-02-01 2007-09-11 Astrazeneca Ab Quinazoline compounds
US7435823B2 (en) 2004-01-23 2008-10-14 Amgen Inc. Compounds and methods of use
US7626030B2 (en) 2004-01-23 2009-12-01 Amgen Inc. Compounds and methods of use
US7652009B2 (en) 2004-11-30 2010-01-26 Amgem Inc. Substituted heterocycles and methods of use
US7795254B2 (en) 2007-10-29 2010-09-14 Amgen Inc. Benzomorpholine derivatives and methods of use
US7858623B2 (en) 2005-04-27 2010-12-28 Amgen Inc. Substituted amide derivatives and methods of use
US20110028478A1 (en) * 2009-05-18 2011-02-03 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
US8765735B2 (en) 2009-05-18 2014-07-01 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
WO2014093230A3 (fr) * 2012-12-10 2014-08-28 Merck Patent Gmbh Compositions et procédés de fabrication de composés pyrimidine et pyridine ayant une activité inhibitrice de btk
US8859570B2 (en) 2003-12-24 2014-10-14 Astrazeneca Ab Maleate salts of a quinazoline derivative useful as an antiangiogenic agent
US8927551B2 (en) 2009-05-18 2015-01-06 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
CN108290838A (zh) * 2015-09-18 2018-07-17 科研制药株式会社 双芳基衍生物和含有其的药物
WO2022004702A1 (fr) * 2020-06-30 2022-01-06 住友化学株式会社 PROCÉDÉ DE LUTTE CONTRE LE CHAMPIGNON DE LA ROUILLE DU SOJA PRÉSENTANT UNE RÉSISTANCE AUX FONGICIDES QoI

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JP4607419B2 (ja) * 2002-11-14 2011-01-05 日本エンバイロケミカルズ株式会社 キノキサリン系化合物またはその塩、および、工業用殺菌組成物
JP2005314259A (ja) * 2004-04-28 2005-11-10 Japan Enviro Chemicals Ltd キノキサリン系化合物またはその塩、および、工業用殺菌組成物
TW200803740A (en) 2005-12-16 2008-01-16 Du Pont 5-aryl isoxazolines for controlling invertebrate pests
TWI412322B (zh) 2005-12-30 2013-10-21 Du Pont 控制無脊椎害蟲之異唑啉
US8623875B2 (en) 2007-06-13 2014-01-07 E.I. Du Pont De Nemours And Company Isoxazoline insecticides
TWI430995B (zh) 2007-06-26 2014-03-21 Du Pont 萘異唑啉無脊椎有害動物控制劑
BRPI0810929B8 (pt) 2007-06-27 2022-12-06 Du Pont uso de um composto de fórmula 1
TWI461411B (zh) 2007-08-17 2014-11-21 Du Pont 製備５－鹵烷基－４，５－二氫異唑衍生物之方法
US8367584B2 (en) 2007-10-03 2013-02-05 E.I. Du Pont De Nemours And Company Naphthalene isoxazoline compounds for control of invertebrate pests
TWI518076B (zh) 2008-04-09 2016-01-21 杜邦股份有限公司 製備雜環化合物之方法
AR076687A1 (es) * 2009-05-18 2011-06-29 Infinity Pharmaceuticals Inc Isoxazolinas como inhibidores de la amidahidrolasa de acidos grasos y com-posiciones farmaceuticas que los contienen
HUE028501T2 (en) 2010-05-27 2016-12-28 Du Pont 4- [5- [3-Chloro-5- (trifluoromethyl) phenyl] -4,5-dihydro-5- (trifluoromethyl) -3-isoxazolyl] -N- [2-oxo-2 - [(2.2, 2-Trifluoroethyl) amino] ethyl] -1-naphthalenecarboxamide crystalline form
JP6469272B2 (ja) * 2017-03-01 2019-02-13 科研製薬株式会社 ビアリール誘導体又はその塩からなる医薬
UY39653A (es) * 2021-03-05 2022-09-30 Sumitomo Chemical Co Compuesto de anillo condensado y uso del mismo.

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0178826A2 (fr) * 1984-10-19 1986-04-23 Zeneca Limited Fongicides
EP0267734A2 (fr) * 1986-11-11 1988-05-18 Zeneca Limited Composés chimiques
EP0538097A1 (fr) * 1991-10-11 1993-04-21 Roussel Uclaf Nouveaux dérivés de l'acide 1-naphtalène acétique, leur procédé de préparation et leur application comme pesticides
EP0566455A1 (fr) * 1992-04-14 1993-10-20 Roussel Uclaf Nouveaux dérivés de l'acide 7-éthynyl alpha-(méthoxyméthylène) 1-naphtalène acétique, leur procédé de préparation et leur application comme pesticides
WO1994023576A1 (fr) * 1993-04-15 1994-10-27 Roussel Uclaf UTILISATION DE DERIVES DE L'ACIDE 7-ETHYNYL α-(METHOXYMETHYLENE) 1-NAPHTALENE ACETIQUE POUR LA PREPARATION DE COMPOSITIONS FONGICIDES
WO1995030639A1 (fr) * 1994-05-09 1995-11-16 Hoechst Schering Agrevo S.A. NOUVEAUX DERIVES DE L'ACIDE β-METHOXY ACRYLIQUE, LEUR PROCEDE DE PREPARATION ET LEUR APPLICATION COMME PESTICIDES

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0178826A2 (fr) * 1984-10-19 1986-04-23 Zeneca Limited Fongicides
EP0267734A2 (fr) * 1986-11-11 1988-05-18 Zeneca Limited Composés chimiques
EP0538097A1 (fr) * 1991-10-11 1993-04-21 Roussel Uclaf Nouveaux dérivés de l'acide 1-naphtalène acétique, leur procédé de préparation et leur application comme pesticides
EP0566455A1 (fr) * 1992-04-14 1993-10-20 Roussel Uclaf Nouveaux dérivés de l'acide 7-éthynyl alpha-(méthoxyméthylène) 1-naphtalène acétique, leur procédé de préparation et leur application comme pesticides
WO1994023576A1 (fr) * 1993-04-15 1994-10-27 Roussel Uclaf UTILISATION DE DERIVES DE L'ACIDE 7-ETHYNYL α-(METHOXYMETHYLENE) 1-NAPHTALENE ACETIQUE POUR LA PREPARATION DE COMPOSITIONS FONGICIDES
WO1995030639A1 (fr) * 1994-05-09 1995-11-16 Hoechst Schering Agrevo S.A. NOUVEAUX DERIVES DE L'ACIDE β-METHOXY ACRYLIQUE, LEUR PROCEDE DE PREPARATION ET LEUR APPLICATION COMME PESTICIDES

Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998005652A2 (fr) * 1996-08-01 1998-02-12 E.I. Du Pont De Nemours And Company Amides cycliques arthropodicides et fongicides
WO1998005652A3 (fr) * 1996-08-01 1998-06-11 E I De Pount De Nemours And Co Amides cycliques arthropodicides et fongicides
CN100360505C (zh) * 1999-02-10 2008-01-09 阿斯特拉曾尼卡有限公司 中间体化合物、它们在制备喹唑啉衍生物中的用途以及它们的制备方法
EP1553097A1 (fr) * 1999-02-10 2005-07-13 AstraZeneca AB Derives de quinazoline utilises comme inhibiteurs de l'angiogenese et produits intermediares
US7074800B1 (en) 1999-02-10 2006-07-11 Astrazeneca Ab Quinazoline derivatives as angiogenesis inhibitors
WO2000047212A1 (fr) * 1999-02-10 2000-08-17 Astrazeneca Ab Derives de quinazoline utilises comme inhibiteurs de l'angiogenese
KR100838617B1 (ko) * 1999-02-10 2008-06-16 아스트라제네카 아베 혈관형성 억제제로서의 퀴나졸린 유도체
EP2050744A1 (fr) * 1999-02-10 2009-04-22 AstraZeneca AB Dérivés de la quinazoline comme inhibiteurs de l'angiogénèse
US8492560B2 (en) 1999-02-10 2013-07-23 Astrazeneca Ab Quinazoline derivatives as angiogenesis inhibitors
CZ303692B6 (cs) * 1999-02-10 2013-03-13 Astrazeneca Ab Chinazolinové deriváty jako inhibitory angiogeneze
US7268230B2 (en) 2002-02-01 2007-09-11 Astrazeneca Ab Quinazoline compounds
US8293902B2 (en) 2002-02-01 2012-10-23 Astrazeneca Ab Quinazoline compounds
US9890140B2 (en) 2003-12-24 2018-02-13 Astrazeneca Ab Maleate salts of a quinazoline derivative useful as an antiangiogenic agent
US9556151B2 (en) 2003-12-24 2017-01-31 Astrazeneca Ab Maleate salts of a quinazoline derivative useful as an antiangiogenic agent
US8859570B2 (en) 2003-12-24 2014-10-14 Astrazeneca Ab Maleate salts of a quinazoline derivative useful as an antiangiogenic agent
US8178557B2 (en) 2004-01-23 2012-05-15 Amgen Inc. Compounds and methods of use
US7435823B2 (en) 2004-01-23 2008-10-14 Amgen Inc. Compounds and methods of use
US7626030B2 (en) 2004-01-23 2009-12-01 Amgen Inc. Compounds and methods of use
US7652009B2 (en) 2004-11-30 2010-01-26 Amgem Inc. Substituted heterocycles and methods of use
US7858623B2 (en) 2005-04-27 2010-12-28 Amgen Inc. Substituted amide derivatives and methods of use
US8685983B2 (en) 2005-04-27 2014-04-01 Amgen Inc. Method of treating cancer with substituted amide derivatives
US8088794B2 (en) 2005-04-27 2012-01-03 Amgen Inc. Substituted amide derivatives and methods of use
US7795254B2 (en) 2007-10-29 2010-09-14 Amgen Inc. Benzomorpholine derivatives and methods of use
US8927551B2 (en) 2009-05-18 2015-01-06 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
US9149465B2 (en) * 2009-05-18 2015-10-06 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
US8765735B2 (en) 2009-05-18 2014-07-01 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
US20110028478A1 (en) * 2009-05-18 2011-02-03 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
WO2014093230A3 (fr) * 2012-12-10 2014-08-28 Merck Patent Gmbh Compositions et procédés de fabrication de composés pyrimidine et pyridine ayant une activité inhibitrice de btk
CN108290838A (zh) * 2015-09-18 2018-07-17 科研制药株式会社 双芳基衍生物和含有其的药物
US10647675B2 (en) 2015-09-18 2020-05-12 Kaken Pharmaceutical Co., Ltd. Biaryl derivative and medicine containing same
AU2016325143B2 (en) * 2015-09-18 2020-08-13 Kaken Pharmaceutical Co., Ltd. Biaryl derivative and medicine containing same
RU2760373C2 (ru) * 2015-09-18 2021-11-24 Какен Фармасьютикал Ко., Лтд. Биарильное производное и содержащее его лекарственное средство
CN108290838B (zh) * 2015-09-18 2021-12-31 科研制药株式会社 双芳基衍生物和含有其的药物
WO2022004702A1 (fr) * 2020-06-30 2022-01-06 住友化学株式会社 PROCÉDÉ DE LUTTE CONTRE LE CHAMPIGNON DE LA ROUILLE DU SOJA PRÉSENTANT UNE RÉSISTANCE AUX FONGICIDES QoI

Also Published As

Publication number Publication date
GB9505651D0 (en) 1995-05-10
IL117595A0 (en) 1996-07-23
ZA962319B (en) 1996-10-30
AU5116096A (en) 1996-10-08
EP0819111A1 (fr) 1998-01-21
JPH11503114A (ja) 1999-03-23

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