WO1993024484A1 - 2-arylpyrroles substitues - Google Patents

2-arylpyrroles substitues Download PDF

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Publication number
WO1993024484A1
WO1993024484A1 PCT/EP1993/001230 EP9301230W WO9324484A1 WO 1993024484 A1 WO1993024484 A1 WO 1993024484A1 EP 9301230 W EP9301230 W EP 9301230W WO 9324484 A1 WO9324484 A1 WO 9324484A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
alkoxy
carbonyl
substituted
halogen
Prior art date
Application number
PCT/EP1993/001230
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German (de)
English (en)
Inventor
Hermann Uhr
Albrecht Marhold
Peter Andres
Christoph Erdelen
Ulrike Wachendorff-Neumann
Wilhelm Stendel
Original Assignee
Bayer Aktiengesellschaft
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Filing date
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Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Publication of WO1993024484A1 publication Critical patent/WO1993024484A1/fr

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Classifications

    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring

Definitions

  • the present invention relates to new substituted 2-arylpyrroles, intermediates for their preparation and their use for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in the forests, in the protection of stocks and materials and in the hygiene sector . It has already become known that structurally similar cyanopyrroles are effective as molluscicides, fungicides and insecticides (see, for example, EP-A
  • R 1 represents cyano or nitro
  • X 1 , X 2 , X 3 and X 4 may be the same or different
  • R 4 represents halogen and n represents a number from 0 to 3
  • R 3 represents hydrogen, phenyl or optionally
  • R 5 and R 6 independently of one another for hydrogen, in each case optionally substituted alkyl
  • Y 1 represents halogen and Y 2 represents halogen, alkyl or haloalkyl.
  • R 1 is cyano or nitro
  • R 2 for the residues
  • X 1 , X 2 , X 3 and X 4 may be the same or different
  • R 4 represents halogen and n represents a number from 0 to 3
  • R 3 represents hydrogen, phenyl or optionally substituted alkyl
  • R 5 and R 6 independently of one another for hydrogen
  • Y 2 represents halogen, alkyl or shark ogenalkyl, is obtained if
  • R 1 , R 2 , Y 1 and Y 2 have the meaning given above, with compounds of the formula (III)
  • R 3 , R 5 and R 6 have the meaning given above and
  • X 6 represents an anionic leaving group, if appropriate in the presence of bases and / or if appropriate in the presence of diluents
  • the new substituted 2-arylpyrroles according to the invention are defined by the general formula (I).
  • wöbei X 1 , X 2 , X 3 and X 4 may be the same or different and represent hydrogen, halogen or
  • R 4 represents halogen and n represents a number from 0 to 3
  • R 3 represents hydrogen, phenyl or C 1 -C 8 alkyl
  • R 5 and R 6 independently of one another represent hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -alkeny 1 or C 3 -C 8 -alkynyl1, the alkyl, alkenyl or alkynyl radicals optionally being represented by 1 to 6 identical or different radicals of the series halogen, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, (C 1 -C 6 alkyl) carbonyloxy, (C 1 -C 6 alkoxy) carbonyl, optionally substituted
  • Phenyl, cyano or nitro are substituted, or represent (C 1 -C 8 alkoxy) carbonyl, (C 1 -C 8 alkenoxy) carbonyl or (C 3 -C 8 alkynoxy) carbonyl, the alkoxy -, Alkenoxy or alkynoxy, optionally by 1 to 6 identical or different radicals from the series halogen, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, (C 1 -C 6 alkyl) carbonyloxy, (C 1 -C 6 -A-koxy) -carbonyl, optionally substituted phenyl, cyano or nitro are substituted, or wherein R 5 and R 6 represent (C 1 -C 8 alkyl) carbonyl, which is optionally substituted by 1 to 6 identical or different radicals from the series halogen, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, (C 1 -C 6 alkyl) carbon
  • Y 2 for fluorine, chlorine, bromine, iodine, C 1 -C 4 alkyl or
  • wöbei X 1 , X 2 , X 3 and X 4 can be the same or different and represent hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl,
  • R 4 represents fluorine, chlorine or bromine and n represents a number from 0 to 2
  • R 3 represents hydrogen, phenyl or C 1 -C 6 alkyl, which is optionally substituted by 1 to 5 fluorine and / or chlorine atoms, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, (C 1 -C 4 - alkyl) carbonyloxy, (C 1 -C 4 alkoxy) carbonyl, phenyl, cyano or nitro,
  • R 5 and R 6 independently of one another represent hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, the alkyl, alkenyl or alkynyl radicals optionally being represented by 1 to 5 Radicals of the series fluorine, chlorine, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, (C 1 -C 4 alkyl) carbonyloxy, (C 1 -C 4 alkoxy) carbonyl, optionally substituted phenyl, Cyano or
  • Alkenoxy or alkynoxy part optionally with 1 to 5 radicals from the series fluorine, chlorine, C 1 -C 4 -alkoxy,
  • C 1 -C 4 alkylthio, (C 1 -C 4 alkyl) carbonyloxy, (C 1 -C 4 alkoxy) carbonyl, optionally substituted Phenyl, cyano or nitro are substituted, or represent (C 1 -C 6 alkyl) carbonyl, which may be by 1 to 5 fluorine and / or chlorine atoms, C 1 -C 4 alkoxy, C 1 -C 4 - Alkylthio, (C 1 -C 4 alkyl) carbonyloxy, (C 1 -C 4 alkoxy) carbonyl, optionally substituted phenyl, cyano or nitro, or where the radicals R 5 and R 6 together with those enclosed by them Nitrogen atoms form a 4- to 6-membered ring, Y 1 represents chlorine or bromine and
  • Y 2 represents chlorine, bromine or CF 3 .
  • halogen in particular fluorine, chlorine, bromine, C 1 -C 4 alkyl and C 1 -C 4 alkoxy.
  • R 1 , R 2 , Y 1 and Y have the meaning given above, are known (DE-A 4 117 752) and / or can be prepared by methods known in principle (see, for example,
  • the starting materials of the general formula (III) used in the production process are known and / or can be prepared by methods known in principle (see, for example, KG Siver et al., J. Pharm. Sei, 79, 66 (1990)).
  • the process of making compounds of the general formula (III) used in the production process are known and / or can be prepared by methods known in principle (see, for example, KG Siver et al., J. Pharm. Sei, 79, 66 (1990)).
  • the process of making compounds of the general formula (III) used in the production process are known and / or can be prepared by methods known in principle (see, for example, KG Siver et al., J. Pharm. Sei, 79, 66 (1990)).
  • Formula (I) is characterized in that compounds of the formula (II) with compounds of the formula
  • inert organic solvents are suitable as diluents in the process according to the invention. These preferably include hydrocarbons such as
  • Benzene, toluene, xylene, further ethers such as dibutyl ether, tert. -Butyl methyl ether, tetrahydrofuran, dioxane, and also polar solvents, such as dimethyl sulfoxide, acetonitrile, sulfolane, dimethyl formamide and N-methyl-pyrrolidone. All conventional proton acceptors can be used as bases in the process according to the invention.
  • Alkali metal and alkaline earth imetal 1-oxides, hydroxides and carbonates such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which can also be used in the presence of phase transfer catalysts such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide or 18- Krone-6 can be used.
  • phase transfer catalysts such as, for example, triethylbenzylammonium chloride, tetrabutylammonium bromide or 18- Krone-6 can be used.
  • Alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butylate, can also be used.
  • the reaction temperatures can be varied within a wide range when carried out. In general, temperatures between -10 ° C and 200 ° C, preferably between 0 ° C and 120 ° C, the reaction components of the formula (II), the deprotonating bases and the components of the formula (III) generally in approximately equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
  • the process is generally carried out under normal pressure, but it can also be carried out under pressure.
  • substituted 2-arylpyrroles (I) according to the invention are suitable for combating, with good plant tolerance and favorable warm-blood toxicity
  • insects especially insects
  • the pests mentioned above include: From the order of the Isopoda, for example Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Symphyla e.g. Scutigerella immaculate.
  • Thysanura e.g. Lepisma saccharina.
  • Periplaneta americana Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis,
  • Dysdercus intermedius Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp. From the order of the Homoptera, for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis
  • Hyalopterus arundinis Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalos iphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus,
  • Nilaparvata lugens Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.
  • Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimat ⁇ bia brumata, Lithocolletis blancardel la, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.
  • Spodoptera spp Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophi la pseudospretella,
  • Attagenus spp. Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealand.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Chrysomyia spp. Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp «, Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyatitis hyoscyami capitata, Dacus oleae, Tipula paludosa.
  • Siphonaptera From the order of the Siphonaptera, for example, Xenopsylla cheopis, Ceratophy1 lus spp ..
  • Acarina for example Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyl locoptruta oleivora, Boophilus spp., Rhipi cephalus spp., Amblyomma spp., Hyalomma spp.,
  • the substituted 2-aryipyrroles (I) according to the invention not only act against plant, hygiene and Storage pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tortoise ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitizing
  • the substituted 2-arylpyrroles (I) according to the invention are notable for high insecticidal activity. They can be used with good success against plant-damaging insects, for example against the
  • the active compounds according to the invention show not only protective but also leaf-systemic and root-systemic properties.
  • substituted 2-aryipyrroles (I) according to the invention are also suitable for controlling soil insects and can be used, for example, to control the maggots of the onion fly (Phorbia antiqua) in the soil.
  • substituted 2-arylpyrroles (I) according to the invention have a high activity against pests of hygiene and pests and can be used, for example, to control the German cockroach (Blattella germanica).
  • the substituted 2-arylpyrroles (I) according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances and in coating compositions for seeds, also in formulations with fuel sets, such as
  • formulations are made in a known manner, e.g. by mixing the substituted 2-arylpyrroles (I) according to the invention with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents
  • Agents ie emulsifiers and t or dispersants and / or foam-generating agents.
  • emulsifiers ie emulsifiers and t or dispersants and / or foam-generating agents.
  • water as an extender can e.g. also organic solvents as auxiliary solvents
  • liquid solvents aromatics, such as xylene, toluene, or Alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes,
  • Hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl formamide and dimethyl sulfoxide, and water;
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; as solid carriers are possible: e.g.
  • natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates;
  • Solid carriers for granulates are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic
  • emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g.
  • Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the substituted 2-arylpyrroles (I) according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active compounds such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others
  • the substituted 2-arylpyrroles (I) according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active ingredient concentration of the use forms can be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.
  • the application is carried out in a manner custom-adapted to the application .
  • the active substances When used against hygiene pests and pests of stored products, the active substances are distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
  • the 2-arylpyrroles (I) substituted according to the invention are also suitable for controlling insects, mites, ticks, etc. in the field of animal husbandry and
  • the use of the substituted 2-arylpyrroles (I) according to the invention takes place in this field in a known manner, such as by oral use in the form of, for example, tablets, capsules, waterings, granules, by dermal or external use in the form of, for example, immersion (dipping), spraying (Spraying), pouring (pour-on and spot-on) and powdering as well as by parenteral application in the form of, for example
  • Shaped body (collar, ear tag) possible.
  • the crude product is purified by chromatography on silica gel (eluent: methylene chloride).
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by dipping them into the active ingredient preparation of the desired concentration and populated with caterpillars of the cabbage cockroach (Plutella maculipennis) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0 V. means that no caterpillars have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Bean plants Phaseolus vulgaris which are heavily infested with all stages of development of the common spider mite or bean spider mite (Tetranychus urticae) are sprayed to runoff point with an active ingredient preparation of the desired concentration. After the desired time, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.

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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

L'invention concerne de nouveaux 2-arylpyrroles substitués de la formule (I) dans laquelle Y?1, Y2, R1, R2, R3, R5 et R6¿ ont la notation donnée dans le descriptif. L'invention concerne en outre un procédé visant à les produire. Les nouveaux 2-arylpyrroles sont utilisés comme pesticides.
PCT/EP1993/001230 1992-05-29 1993-05-17 2-arylpyrroles substitues WO1993024484A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4217725.1 1992-05-29
DE19924217725 DE4217725A1 (de) 1992-05-29 1992-05-29 Substituierte 2-Arylpyrrole

Publications (1)

Publication Number Publication Date
WO1993024484A1 true WO1993024484A1 (fr) 1993-12-09

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PCT/EP1993/001230 WO1993024484A1 (fr) 1992-05-29 1993-05-17 2-arylpyrroles substitues

Country Status (3)

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AU (1) AU4069193A (fr)
DE (1) DE4217725A1 (fr)
WO (1) WO1993024484A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006128692A2 (fr) * 2005-06-01 2006-12-07 Ucb Pharma, S.A. Derives de 2-oxo-1-pyrrolidine
CN105622598A (zh) * 2016-02-26 2016-06-01 河南好年景生物发展有限公司 用于杀虫的芳基吡咯腈类化合物及制备方法和用途以及农用杀虫剂及防治害虫方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0312723A2 (fr) * 1987-10-23 1989-04-26 American Cyanamid Company Procédé et appâts pour lutter contre les mollusques
EP0347488A1 (fr) * 1988-06-23 1989-12-27 American Cyanamid Company Arylpyrroles comme agents insecticides, acaricides et nématicides et procédé pour leur préparation
EP0358047A2 (fr) * 1988-09-08 1990-03-14 American Cyanamid Company Procédé de lutte contre les champignons phytopathogènes
EP0492171A1 (fr) * 1990-12-26 1992-07-01 American Cyanamid Company 2-Aryl-5-triflurométhyl-2-pyrrolines, et procédé pour la préparation des 2-aryl-1-(alkoxyméthyl)-4-halo-5-(triflurométhyl)pyrroles insecticides
EP0515941A1 (fr) * 1991-05-30 1992-12-02 Bayer Ag 2-Arylpyrroles substitués
EP0530147A1 (fr) * 1991-08-28 1993-03-03 Ciba-Geigy Ag 3-Cyano-2-phényl-pyrroles comme pesticides
EP0530515A1 (fr) * 1991-09-06 1993-03-10 American Cyanamid Company N-alkanoylaminométhyl et N-aroylaminométhyl pyrrole insecticides et acaricides

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0312723A2 (fr) * 1987-10-23 1989-04-26 American Cyanamid Company Procédé et appâts pour lutter contre les mollusques
EP0347488A1 (fr) * 1988-06-23 1989-12-27 American Cyanamid Company Arylpyrroles comme agents insecticides, acaricides et nématicides et procédé pour leur préparation
EP0358047A2 (fr) * 1988-09-08 1990-03-14 American Cyanamid Company Procédé de lutte contre les champignons phytopathogènes
EP0492171A1 (fr) * 1990-12-26 1992-07-01 American Cyanamid Company 2-Aryl-5-triflurométhyl-2-pyrrolines, et procédé pour la préparation des 2-aryl-1-(alkoxyméthyl)-4-halo-5-(triflurométhyl)pyrroles insecticides
EP0515941A1 (fr) * 1991-05-30 1992-12-02 Bayer Ag 2-Arylpyrroles substitués
EP0530147A1 (fr) * 1991-08-28 1993-03-03 Ciba-Geigy Ag 3-Cyano-2-phényl-pyrroles comme pesticides
EP0530515A1 (fr) * 1991-09-06 1993-03-10 American Cyanamid Company N-alkanoylaminométhyl et N-aroylaminométhyl pyrrole insecticides et acaricides

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006128692A2 (fr) * 2005-06-01 2006-12-07 Ucb Pharma, S.A. Derives de 2-oxo-1-pyrrolidine
WO2006128692A3 (fr) * 2005-06-01 2007-03-15 Ucb Sa Derives de 2-oxo-1-pyrrolidine
CN105622598A (zh) * 2016-02-26 2016-06-01 河南好年景生物发展有限公司 用于杀虫的芳基吡咯腈类化合物及制备方法和用途以及农用杀虫剂及防治害虫方法
WO2017143872A1 (fr) * 2016-02-26 2017-08-31 河南好年景生物发展有限公司 Composé pesticide d'aryle pyrrole nitrile, son procédé de préparation, ses utilisations, pesticide agricole, et procédé de régulation des ravageurs
CN105622598B (zh) * 2016-02-26 2017-12-22 河南好年景生物发展有限公司 用于杀虫的芳基吡咯腈类化合物及制备方法和用途以及农用杀虫剂及防治害虫方法

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DE4217725A1 (de) 1993-12-02
AU4069193A (en) 1993-12-30

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