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WO1999007687A1 - Derives pesticides de 4-benzyl-1,2,4-triazolin-5-one - Google Patents

Derives pesticides de 4-benzyl-1,2,4-triazolin-5-one Download PDF

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Publication number
WO1999007687A1
WO1999007687A1 PCT/GB1998/002238 GB9802238W WO9907687A1 WO 1999007687 A1 WO1999007687 A1 WO 1999007687A1 GB 9802238 W GB9802238 W GB 9802238W WO 9907687 A1 WO9907687 A1 WO 9907687A1
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Prior art keywords
optionally substituted
chr
compounds
compound
substituted alkyl
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English (en)
Inventor
Peter John West
David Stephen Carver
Ian Paul Cooper
Peter Stuart Gates
Donald James Simpson
Richard Michael Turner
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Bayer CropScience Ltd Great Britain
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Agrevo UK Ltd
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Priority to AU86352/98A priority Critical patent/AU8635298A/en
Publication of WO1999007687A1 publication Critical patent/WO1999007687A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • 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
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • C07D409/10—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 aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • 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
    • C07D413/10—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 carbon chain containing aromatic rings
    • 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
    • C07D417/10—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 linked by a carbon chain containing aromatic rings
    • 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
    • C07D417/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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 compounds having pesticidal, especially fungicidal, insecticidal and acaricidai, activity.
  • the invention provides compounds of general formula I
  • R1 is optionally substituted alkyl
  • R 2 is optionally substituted alkyl, halogen, -OR 4 , -SR 4 , -S(O)R 4 , -S(O)2R 4 or
  • R 7 and R 7a which may be the same or different are, optionally substituted alkyl, acyl, halogen or cyano;
  • L is optionally substituted alkyl; optionally substituted alkenyl; optionally substituted alkynyl; optionally substituted heterocyclyl; optionally substituted carbocyclyl, preferably optionally substituted phenyl; or Si(R 1 5) 3 ; or one R 3 , K and L, together with the phenyl ring M, form an optionally substituted fused ring, which may contain heteroatoms; where R 4 is hydrogen or optionally substituted alkyl;
  • R5 and Rp which may be the same or different, are hydrogen or optionally substituted alkyl, or R5 and R 8 taken together with the nitrogen to which they are attached may form a heterocyclyl group, preferably a 5 to 7-membered heterocyclyl group, which may be substituted and may contain other hetero atoms, for example morpholino, thiomorpholino or piperidinyl; p is 0 to 2;
  • A1 is -O-, -S-, -NR 8 - or -O-N(R 8 )-;
  • a 2 is O, S or NR 8 ;
  • a 3 is -O-, -S-, -NR 8 - or a direct bond;
  • R 8 is hydrogen, optionally substituted alkyl, optionally substituted carbocyclyl or optionally substituted heterocyclyl
  • R 9 and R 12 which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, -NR 5 R 6 , cyano, halogen or nitro;
  • R11 is hydrogen, optionally substituted alkyl or optionally substituted carbocyclyl
  • R 5 is alkyl.
  • Some novel compounds of general formula I have weak pesticidal activity but still have utility as intermediates and such compounds also form part of the invention. Therefore, according to another aspect the invention provides as reaction intermediates, compounds of formula II, wherein Q D is a leaving group, preferably a halogen such as bromine, and R 1 , R 2 , R 3 , R 7 and R 7a are as defined above.
  • the invention provides as reaction intermediates, compounds of formula III, wherein R 1 , R 3 , R 7 , R 7a , L and K are as defined above.
  • Any alkyl group present in the molecule may be straight or branched and is preferably of 1 to 10 carbon atoms, especially 1 to 7 and particularly 1 to 5 carbon atoms.
  • Any alkenyl or alkynyl group may be straight or branched and is preferably of 2 to 7 carbon atoms and up to 3 double or triple bonds which may be conjugated, for example vinyl, allyl, butadienyl or propargyl.
  • carbocyclyl or carbocyclic includes saturated carbocyclyl groups; unsaturated carbocyclyl groups having up to 3 double bonds, which may be conjugated; and aromatic carbocyclyl groups, e.g. phenyl.
  • Carbocyclyl groups are typically 3 to 8 membered rings.
  • carbocyclyl includes fused carbocyclyl groups, e.g. napthalene, phenanthrene, indane and indene.
  • heterocyclyl or heterocyclic 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, triazolyl, thiadiazolyl, pyranyl, pyridyl, piperidinyl, dioxanyl, morpholino, dithianyl, thiomo ⁇ holino, pyridaziny
  • heterocyclyl includes fused heterocyclyl groups, for example benzimidazolyl, benzoxazolyl, imidazopyridinyl, benzoxazinyl, benzothiazinyl, oxazolopyridinyl, benzofuranyl, quinolinyl, quinazolinyl, quinoxalinyl, dihydroquinazolinyl, benzothiazolyl, phthalimido, benzofuranyl, benzodiazepinyl, indolyl and isoindolyl.
  • Any alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl group, when substituted, may be substituted by at least one group, which may be the same or different, and may be selected from the group: nitro; halogen; cyano; acyl; -O-acyl; -S-acyl; optionally substituted carbocyclyl; optionally substituted heterocyclyl; -SF5;
  • R a is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl and optionally substituted heterocyclyl; -OR* 3 and -SR 13 where R ⁇ is the same as R a or hydrogen; NR c Rd where R c and R ⁇ , which may be the same or different, are hydrogen, optionally substituted alkyl, acyl, or R c and R d taken together with the nitrogen to which they are attached form a heterocyclyl group, preferably a 5 to 7-membered heterocyclyl group, which may be substituted and may contain other hetero atoms, for example mo ⁇ holino, thiomorpholino or piperidinyl.
  • Any carbocyclyl or heterocyclyl groups may also be substituted by optionally substituted alkyl, optionally substituted alkenyl and optionally substituted alkynyl.
  • Particularly preferred substituents on any alkyl, alkenyl or alkynyl group are halogen, alkoxy, haloalkoxy, alkylthio or optionally substituted phenyl.
  • Particularly preferred substituents on any carbocyclyl or heterocyclyl group are as defined above for alkyl, alkenyl or alkynyl, and also alkyl and haloalkyl.
  • acyl includes the residue of sulfur and phosphorus-containing acids as well as carboxylic acids.
  • R e , R f and R9 which may be the same or different, are as defined for R D hereinabove, or R e and Rf, or Rf and R9, together with the atom(s) to which they are attached may form a ring, preferably a 5 to 7-membered heterocyclyl group which may be substituted and may contain other hetero atoms.
  • 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 (P/asmopara viticola), rice blast (Pyricu/aria oryzae), cereal eyespot (Pseudocercospore/la herpotrichoides), rice sheath blight (Pellicularia sasakii), grey mould (Botrytis cinerea), damping off
  • rice blast Pyricu/aria oryzae
  • cereal eyespot Pseudocercospore/la herpotrichoides
  • rice sheath blight Pellicularia 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 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; Coleoptera, including corn rootworms (Diabrotica spp., e.g. Diabrotica undecimpunctata); and spider mites, such as Tetranychus spp..
  • Diptera such as sheep blow-fly, Lucilia sericata, and house-flies, Musca domestica
  • Lepidoptera including Plutella xylostella
  • 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 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 ⁇ /-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
  • 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 % (w/w), especially 0.0001 to 0.01 % (w/w).
  • the amount of active ingredient can vary widely and can be, for example, from 5 to 95 % (w/w) 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.
  • the starting isocyanates IV can prepared in one stage by reacting the corresponding primary amine hydrochloride V with phosgene.
  • Primary amine hydrochloride Va i.e. where R 7 and R a are hydrogen in V, may be prepared according to the following reaction sequence via cyano intermediate VI.
  • Cyano intermediate Via i.e. general intermediate VI where K is -0-, may be prepared by coupling compound VII, where Z is a leaving group for example halogen, with an hydroxy compound VIII.
  • Z is a leaving group for example halogen
  • the reaction conditions are preferably copper in refluxing ethanol.
  • modification of the group -K-L may be performed after construction of the triazole ring.
  • Compounds of formula lc can be converted into further compounds of general formula I.
  • compounds of formula Id where R 2 is -OR 4 can be prepared by reacting lc with a compounds of formula M + ⁇ 0R 4 , where M is a metal.
  • compounds of formula le where R 2 is -SR 4 can be prepared by reacting lc with compounds of formula M + " SR 4 .
  • Modification of the group -K-L can be performed using a number of transformations known to the skilled person, either before or after construction of the five membered heterocycle.
  • compounds of formula Ij i.e. compounds of formula I where K is -O ⁇ C- and L is -Si(R 1 5)g
  • ⁇ is preferably a halogen, especially bromine or iodine, with HC ⁇ CSKR 1 ⁇
  • compounds of formula Ik i.e. compounds of formula I where K is a direct bond and L is an aromatic carbocyclyl or heterocyclyl group, can be prepared by coupling II with a suitable boronic acid derivative.
  • compounds of formula Ip i.e compounds of general formula I where R 2 is SMe, may be prepared according to the following reaction scheme.
  • Typical reaction conditions comprise treating compounds X with a base, such as sodium hydride, followed by addition of XI, where Y a is a leaving group such as halogen.
  • Compounds of formula Iq where R 2 is S(0)Me can be prepared from compounds of formula Ip by treatment with a compound such as monoperoxyphthalic acid magnesium salt hexahydrate in the presence of benzyltriethylammonium chloride.
  • Example 5 4- ⁇ [2-Chloro-5-(3-trifluoromethyl)acetophenoneoximinomethyl]benzyl)-3- methylthio-1 -methyl-4,5-dihydro-1 HA ,2,4-triazol-5-one (compound 62b)
  • 3-trifluoromethylacetophenone oxime 0.6 g
  • dry dimethylformamide 10 ml
  • potassium ferf-butoxide 0.35 g
  • Example 8 Compound 28a The compound was obtained from the product of stage a) below and methyl 2-[(3- trifluoromethylbenzylidenelhydrazinocarbodithioate using analogous methodology to Example 4.
  • Compounds are assessed for activity against one or more of the following:
  • Phytophthora infestans late tomato blight
  • Plasmopara viticola vine downy mildew
  • 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. In the case of volatile compounds the plants are covered to hinder loss of the compound. After an appropriate time, the degree of infection of the affected part of the plant was visually estimated. Compounds were assessed on a score of 1 to 3 where 1 is little or no control, 2 is moderate control and 3 is good to total control. At a concentration of 500 ppm (w/v) or less, the following compounds scored 2 or more against the fungi specified.
  • Leptosphaeria nodorum Leptosphaeria nodorum.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth 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)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Composés répondant à la formule générale (I) et possédant une activité pesticide, et en particulier, des activités fongicide, insecticide et acaricide.
PCT/GB1998/002238 1997-08-05 1998-08-05 Derives pesticides de 4-benzyl-1,2,4-triazolin-5-one Ceased WO1999007687A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU86352/98A AU8635298A (en) 1997-08-05 1998-08-05 Pesticidal 4-benzyl-1,2,4-triazolin-5-one derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9716446.1A GB9716446D0 (en) 1997-08-05 1997-08-05 Fungicides
GB9716446.1 1997-08-05

Publications (1)

Publication Number Publication Date
WO1999007687A1 true WO1999007687A1 (fr) 1999-02-18

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ID=10816937

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1998/002238 Ceased WO1999007687A1 (fr) 1997-08-05 1998-08-05 Derives pesticides de 4-benzyl-1,2,4-triazolin-5-one

Country Status (3)

Country Link
AU (1) AU8635298A (fr)
GB (1) GB9716446D0 (fr)
WO (1) WO1999007687A1 (fr)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000007999A1 (fr) * 1998-08-03 2000-02-17 Sumitomo Chemical Company, Limited Derives de triazolone, leur utilisation, et produits intermediaires obtenus a partir de ces derives
WO2001011966A1 (fr) * 1999-08-18 2001-02-22 Aventis Cropscience Gmbh Compositions fongicides
WO2001012604A1 (fr) * 1999-08-18 2001-02-22 Aventis Cropscience Gmbh Fongicides
WO2001042227A1 (fr) * 1999-12-08 2001-06-14 Sumitomo Chemical Company, Limited Composes de difluoromethyltriazolone, utilisation de ces composes et intermediaires pour leur fabrication
WO2004105488A1 (fr) * 2003-05-27 2004-12-09 Basf Aktiengesellschaft Derives de l'hydrazone combattant les insectes et arachnides nuisibles
WO2009158011A1 (fr) * 2008-06-26 2009-12-30 Amgen Inc. Alcools d’alcynyle utilisés comme inhibiteurs de kinases
CN101790313A (zh) * 2007-06-06 2010-07-28 葛兰素史密丝克莱恩有限责任公司 化合物
US8686007B2 (en) 2011-04-22 2014-04-01 Cytokinetics, Inc. Certain heterocycles, compositions thereof, and methods for their use
WO2014207052A1 (fr) * 2013-06-27 2014-12-31 Basf Se Composés de type strobilurine pour lutter contre les champignons phytopathogènes
US8946202B2 (en) 1999-01-25 2015-02-03 Aeolus Sciences, Inc. Substituted porphyrins
WO2015191382A1 (fr) * 2014-06-11 2015-12-17 E. I. Du Pont De Nemours And Company Tétrazolinones fongicides
US9604965B2 (en) 2010-04-23 2017-03-28 Cytokinetics, Inc. Substituted pyridazines as skeletal muscle modulators
US9730886B2 (en) 2010-04-23 2017-08-15 Cytokinetics, Inc. Amino-pyrimidine skeletal muscle modulators
WO2018011111A1 (fr) 2016-07-12 2018-01-18 Bayer Cropscience Aktiengesellschaft Composés bicycliques utilisés comme pesticides
US9994528B2 (en) 2010-04-23 2018-06-12 Cytokinetics, Inc. Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use
WO2019050026A1 (fr) * 2017-09-11 2019-03-14 住友化学株式会社 Composé tétrazolinone et son utilisation
WO2021153782A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 PROCÉDÉ DE LUTTE CONTRE PHAKOPSORA PACHYRHIZI QUI PRÉSENTE UNE RÉSISTANCE CONTRE LE FONGICIDE QoI
US11382895B2 (en) 2008-05-23 2022-07-12 National Jewish Health Methods for treating injury associated with exposure to an alkylating species

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EP0412594A2 (fr) * 1989-07-28 1991-02-13 Merck & Co. Inc. Triazolinones, triazolinethiones et triazolinimines substituées comme antagonistes d'angiotensine II
WO1991012001A1 (fr) * 1990-02-13 1991-08-22 Merck & Co., Inc. Agents antagonistes de l'angiotensine ii dans lesquels est incorpore un element de benzyle substitue
WO1991018888A1 (fr) * 1990-05-25 1991-12-12 G.D. Searle & Co. Composes de 1,2,4-triazolones a substitution n utilises dans le traitement de troubles cardiovasculaires
EP0475898A1 (fr) * 1990-09-10 1992-03-18 Ciba-Geigy Ag Composés azacycliques
WO1992020662A1 (fr) * 1991-05-10 1992-11-26 Merck & Co., Inc. Derives acides d'aralkyltriazole actifs en tant qu'antagonistes de l'angiotensine ii
WO1996026191A1 (fr) * 1995-02-24 1996-08-29 E.I. Du Pont De Nemours And Company Amides cycliques fongicides
WO1996036615A1 (fr) * 1995-05-16 1996-11-21 E.I. Du Pont De Nemours And Company Amides cycliques fongicides
WO1996036616A1 (fr) * 1995-05-17 1996-11-21 E.I. Du Pont De Nemours And Company Amides cycliques fongicides

Patent Citations (8)

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Publication number Priority date Publication date Assignee Title
EP0412594A2 (fr) * 1989-07-28 1991-02-13 Merck & Co. Inc. Triazolinones, triazolinethiones et triazolinimines substituées comme antagonistes d'angiotensine II
WO1991012001A1 (fr) * 1990-02-13 1991-08-22 Merck & Co., Inc. Agents antagonistes de l'angiotensine ii dans lesquels est incorpore un element de benzyle substitue
WO1991018888A1 (fr) * 1990-05-25 1991-12-12 G.D. Searle & Co. Composes de 1,2,4-triazolones a substitution n utilises dans le traitement de troubles cardiovasculaires
EP0475898A1 (fr) * 1990-09-10 1992-03-18 Ciba-Geigy Ag Composés azacycliques
WO1992020662A1 (fr) * 1991-05-10 1992-11-26 Merck & Co., Inc. Derives acides d'aralkyltriazole actifs en tant qu'antagonistes de l'angiotensine ii
WO1996026191A1 (fr) * 1995-02-24 1996-08-29 E.I. Du Pont De Nemours And Company Amides cycliques fongicides
WO1996036615A1 (fr) * 1995-05-16 1996-11-21 E.I. Du Pont De Nemours And Company Amides cycliques fongicides
WO1996036616A1 (fr) * 1995-05-17 1996-11-21 E.I. Du Pont De Nemours And Company Amides cycliques fongicides

Cited By (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6489487B1 (en) 1998-08-03 2002-12-03 Sumitomo Chemical Company, Limited Triazolone derivatives, use thereof, and intermediates therefor
WO2000007999A1 (fr) * 1998-08-03 2000-02-17 Sumitomo Chemical Company, Limited Derives de triazolone, leur utilisation, et produits intermediaires obtenus a partir de ces derives
US9289434B2 (en) 1999-01-25 2016-03-22 Aeolus Sciences, Inc. Substituted porphyrins
US8946202B2 (en) 1999-01-25 2015-02-03 Aeolus Sciences, Inc. Substituted porphyrins
US6939882B1 (en) 1999-08-18 2005-09-06 Aventis Cropsciences Gmbh Fungicides
JP2003507368A (ja) * 1999-08-18 2003-02-25 アベンティス クロップサイエンス ゲゼルシャフト ミット ベシュレンクテル ハフツング 殺真菌剤
US6630495B1 (en) 1999-08-18 2003-10-07 Bayer Cropscience Gmbh Fungicides
WO2001011966A1 (fr) * 1999-08-18 2001-02-22 Aventis Cropscience Gmbh Compositions fongicides
WO2001012604A1 (fr) * 1999-08-18 2001-02-22 Aventis Cropscience Gmbh Fongicides
JP4965779B2 (ja) * 1999-08-18 2012-07-04 バイエル・クロップサイエンス・アーゲー 殺真菌剤
US6762197B2 (en) 1999-12-08 2004-07-13 Sumitomo Chemical Company, Limited Difluoromethyltriazolone compounds, use of the same and intermediates for the production thereof
WO2001042227A1 (fr) * 1999-12-08 2001-06-14 Sumitomo Chemical Company, Limited Composes de difluoromethyltriazolone, utilisation de ces composes et intermediaires pour leur fabrication
WO2004105488A1 (fr) * 2003-05-27 2004-12-09 Basf Aktiengesellschaft Derives de l'hydrazone combattant les insectes et arachnides nuisibles
EP2166856A4 (fr) * 2007-06-06 2012-05-30 Glaxosmithkline Llc Composés chimiques
CN101790313A (zh) * 2007-06-06 2010-07-28 葛兰素史密丝克莱恩有限责任公司 化合物
JP2010529965A (ja) * 2007-06-06 2010-09-02 グラクソスミスクライン エルエルシー 化合物
US11382895B2 (en) 2008-05-23 2022-07-12 National Jewish Health Methods for treating injury associated with exposure to an alkylating species
WO2009158011A1 (fr) * 2008-06-26 2009-12-30 Amgen Inc. Alcools d’alcynyle utilisés comme inhibiteurs de kinases
US9994528B2 (en) 2010-04-23 2018-06-12 Cytokinetics, Inc. Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use
US11369565B2 (en) 2010-04-23 2022-06-28 Cytokinetics, Inc. Amino-pyrimidine skeletal muscle modulators
US10765624B2 (en) 2010-04-23 2020-09-08 Cytokinetics, Inc. Amino-pyrimidine skeletal muscle modulators
US10272030B2 (en) 2010-04-23 2019-04-30 Cytokinetics, Inc. Amino-pyrimidine skeletal muscle modulators
US9604965B2 (en) 2010-04-23 2017-03-28 Cytokinetics, Inc. Substituted pyridazines as skeletal muscle modulators
US9730886B2 (en) 2010-04-23 2017-08-15 Cytokinetics, Inc. Amino-pyrimidine skeletal muscle modulators
US10076519B2 (en) 2010-04-23 2018-09-18 Cytokinetics, Inc. Substituted pyridazines as skeletal muscle modulators
US9278962B2 (en) 2011-04-22 2016-03-08 Cytokinetics, Inc. Certain heterocycles, compositions thereof, and methods for their use
US8759380B2 (en) 2011-04-22 2014-06-24 Cytokinetics, Inc. Certain heterocycles, compositions thereof, and methods for their use
US8686007B2 (en) 2011-04-22 2014-04-01 Cytokinetics, Inc. Certain heterocycles, compositions thereof, and methods for their use
WO2014207052A1 (fr) * 2013-06-27 2014-12-31 Basf Se Composés de type strobilurine pour lutter contre les champignons phytopathogènes
WO2015191382A1 (fr) * 2014-06-11 2015-12-17 E. I. Du Pont De Nemours And Company Tétrazolinones fongicides
WO2018011111A1 (fr) 2016-07-12 2018-01-18 Bayer Cropscience Aktiengesellschaft Composés bicycliques utilisés comme pesticides
WO2019050026A1 (fr) * 2017-09-11 2019-03-14 住友化学株式会社 Composé tétrazolinone et son utilisation
CN111094275A (zh) * 2017-09-11 2020-05-01 住友化学株式会社 四唑啉酮化合物及其用途
JPWO2019050026A1 (ja) * 2017-09-11 2020-10-29 住友化学株式会社 テトラゾリノン化合物およびその用途
US10939681B2 (en) 2017-09-11 2021-03-09 Sumitomo Chemical Company, Limited Tetrazolinone compound and use thereof
JP7050075B2 (ja) 2017-09-11 2022-04-07 住友化学株式会社 テトラゾリノン化合物およびその用途
WO2021153782A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 PROCÉDÉ DE LUTTE CONTRE PHAKOPSORA PACHYRHIZI QUI PRÉSENTE UNE RÉSISTANCE CONTRE LE FONGICIDE QoI
US12439917B2 (en) 2020-01-31 2025-10-14 Sumitomo Chemical Company, Limited Method for controlling phakopsora pachyrhizi having resistance against QoI fungicide

Also Published As

Publication number Publication date
AU8635298A (en) 1999-03-01
GB9716446D0 (en) 1997-10-08

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