EP0000887A1 - Esters et esteramides de pyrimidine-(4) d'acide (thiono)thiol-phosphorique (phosphonique) avec substituant cyclopropyl, leur procédé de préparation et leur application comme insecticides et acaricides - Google Patents

Esters et esteramides de pyrimidine-(4) d'acide (thiono)thiol-phosphorique (phosphonique) avec substituant cyclopropyl, leur procédé de préparation et leur application comme insecticides et acaricides Download PDF

Info

Publication number
EP0000887A1
EP0000887A1 EP78100599A EP78100599A EP0000887A1 EP 0000887 A1 EP0000887 A1 EP 0000887A1 EP 78100599 A EP78100599 A EP 78100599A EP 78100599 A EP78100599 A EP 78100599A EP 0000887 A1 EP0000887 A1 EP 0000887A1
Authority
EP
European Patent Office
Prior art keywords
iso
propyl
butyl
spp
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP78100599A
Other languages
German (de)
English (en)
Other versions
EP0000887B1 (fr
Inventor
Fritz Dr. Maurer
Ingeborg Dr. Hammann
Wolfgang Dr. Behrenz
Wilhelm Dr. Stendel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of EP0000887A1 publication Critical patent/EP0000887A1/fr
Application granted granted Critical
Publication of EP0000887B1 publication Critical patent/EP0000887B1/fr
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen 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
    • 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
    • A01N37/08—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 carboxylic groups or thio analogues thereof, directly attached by the carbon atom to a cycloaliphatic ring; Derivatives thereof
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6509—Six-membered rings
    • C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3

Definitions

  • the present invention relates to new cyclopropyl-substituted pyrimidine (4) yl (thiono) (thiol) -phosphorus (phosphonic) acid esters or ester amides, which have insecticidal and acaricidal properties, and a process for their preparation.
  • 0.0-dialkyl-O-pyrimidinylthionophosphoric acid esters e.g. 0.0-dimethyl-0- [2-ethyl-4-ethoxy-pyrimidine (6) yl] - or 0.0-diethyl-0- [2-isopropyl-4-methyl-pyrimidine (6) ylJ-thionophosphoric acid ester , insecticidal and acaricidal properties (see U.S. Patents 2,754,243 and 3,862,188).
  • the cyclopropyl-substituted pyrimidine (4) yl (thiono) (thiol) -phosphor (phosphonic) acid esters or ester amides have a better insecticidal and acaricidal action than the known pyrimidine (6) yl thionophosphoric acid esters of analogous constitution and same direction of action.
  • the compounds of the present invention thus represent a real enrichment of technology.
  • the 2-cyclopropyl-4-hydroxy-pyrimidines (III) to be used as starting materials can be prepared by processes known from the literature, for example by 2-Cyclopropyl-4,6-dihydroxy-pyrimidine alkylated, e.g. with dimethyl sulfate, and optionally the products obtained are halogenated, e.g. with bromine.
  • the process for the preparation of the compounds according to the invention is preferably carried out using suitable solvents or diluents.
  • suitable solvents or diluents Practically all inert organic solvents can be considered as such. These include in particular aliphatic and aromatic, optionally chlorinated hydrocarbons, such as benzene, toluene, xylene, gasoline, methylene chloride, chloroform, carbon tetrachloride, chlorobenzene, or ether, e.g.
  • ketones for example acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone, and also nitriles, such as aceto and propionitrile.
  • Alkalicarbo have proven particularly useful nates and alcoholates, such as sodium and potassium carbonate, methylate or ethylate, furthermore aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine and pyridine.
  • the reaction temperature can be varied within a wide range. In general, preferably between 0 and loo ° C, at 2o to 6 0 0 c.
  • the reaction is generally allowed to proceed at normal pressure.
  • the starting materials are usually used in an equivalent ratio.
  • An excess of one or the other component has no significant advantages.
  • the reactants are usually combined in one of the solvents mentioned above in the presence of an acid acceptor and stirred at elevated temperature for one or more hours to complete the reaction. Then the mixture is mixed with an organic solvent, e.g. Toluene, and works up the organic phase in the usual way by washing, drying and distilling off the solvent.
  • an organic solvent e.g. Toluene
  • the new compounds are often obtained in the form of oils, which usually cannot be distilled without decomposing, but by so-called “distillation", i.e. can be freed from the last volatile constituents by prolonged heating under reduced pressure to moderately elevated temperatures and can be cleaned in this way.
  • the refractive index is used to characterize them.
  • Some compounds are obtained in crystalline form and are characterized by their melting point.
  • the cyclopropyl-substituted pyrimidine (4) yl (thiono) - (Thiol) -phosphoric (phosphonic) acid esters or -esteramides from an excellent insecticidal and acaricidal action. They act against plant, hygiene and storage pests and in the veterinary medical sector. With low phytotoxicity, they have a good effect against sucking as well as feeding insects and mites.
  • the compounds according to the invention can be successfully used as pesticides in crop protection and in the hygiene, stored product protection and veterinary sectors.
  • Doralis pomi Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleaarvitella, Laataelellaidia Pseudococcus spp. Psylla spp ..
  • Phyllellanistia app Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapaa pomonella, Pieris app., Chilo app., Pyrausta nubilalis, Ephestia kuehniella, Cauleria Capella pellella, Galleria capella pellella Choristoneura fumiferana, Clyaia ambiguella, Homona magnanima, Tortrix viridana. From the order of the Coleoptera z. B.
  • Bibio hortulanus Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, D acus oleae, Tipula paludosa.
  • Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,. Chori ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension emulsion concentrates, seed pu ders, active ingredient-impregnated natural and synthetic substances, fine encapsulations in polymeric substances and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals, etc. as well as ULV cold and warm fog formulations.
  • customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension emulsion concentrates, seed pu ders, active ingredient-impregnated natural and synthetic substances, fine encapsulations in polymeric substances and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals, etc. as well as
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid solvents aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraf fine, for example 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 dimethylformamide and dimethyl sulfoxide, and water;
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; as solid carriers: natural rock flour, such as ka
  • Adhesives such as carboxymethyl cellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention are used in the form of their commercially available formulations and / or the use forms prepared from these formulations.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 100% by weight of active substance, preferably between 0.01 and 10% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active ingredients When used against hygiene pests and pests of stored products, the active ingredients are distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
  • the active compounds according to the invention are used in the veterinary sector in a known manner, such as by oral use in the form of, for example, tablets, capsules, drinkers, granules, by dermal use in the form of, for example, diving (dipping), spraying (spraying), pouring-on and spot-on) and powdering and by parenteral use in the form of, for example, injection.
  • Solvent 3 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • cabbage leaves (Brassica oleracea) are sprayed to runoff point and populated with horseradish leaf beetle larvae (Phaedon cochleariae).
  • the kill is determined in%.
  • the compounds of Examples 1, 3, 6, 9 and 14 have an excellent action which is clearly superior to the action of the compounds known from the prior art.
  • Solvent 3 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the kill is determined in%.
  • the compounds of Examples 2, 3, 4 and 5 have an excellent activity which is clearly superior to that of the compounds known from the prior art.
  • Test animals Sitophilus granarius
  • Solvent acetone
  • the condition of the test animals is checked 3 days after starting the experiments.
  • the death rate is determined in%.
  • Emulsifier 80 parts by weight of Cremophor EL
  • the active substance in question is mixed with the stated solvent in a ratio of 1: 2 and the concentrate thus obtained is diluted with water to the desired concentration.
  • the 2-cyclopropyl-4-hydroxy-pyrimidines to be used as starting materials can e.g. can be produced as follows:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Molecular Biology (AREA)
  • Agronomy & Crop Science (AREA)
  • Biochemistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP78100599A 1977-08-19 1978-08-07 Esters et esteramides de pyrimidine-(4) d'acide (thiono)thiol-phosphorique (phosphonique) avec substituant cyclopropyl, leur procédé de préparation et leur application comme insecticides et acaricides Expired EP0000887B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772737401 DE2737401A1 (de) 1977-08-19 1977-08-19 Cyclopropylsubstituierte pyrimidin (4)yl(thiono)-(thiol)-phosphor(phosphon) -saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE2737401 1977-08-19

Publications (2)

Publication Number Publication Date
EP0000887A1 true EP0000887A1 (fr) 1979-03-07
EP0000887B1 EP0000887B1 (fr) 1980-10-29

Family

ID=6016780

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100599A Expired EP0000887B1 (fr) 1977-08-19 1978-08-07 Esters et esteramides de pyrimidine-(4) d'acide (thiono)thiol-phosphorique (phosphonique) avec substituant cyclopropyl, leur procédé de préparation et leur application comme insecticides et acaricides

Country Status (16)

Country Link
US (1) US4202889A (fr)
EP (1) EP0000887B1 (fr)
JP (1) JPS5441884A (fr)
AU (1) AU516426B2 (fr)
BR (1) BR7805355A (fr)
CA (1) CA1091671A (fr)
CS (1) CS199216B2 (fr)
DD (1) DD138145A5 (fr)
DE (2) DE2737401A1 (fr)
DK (1) DK367678A (fr)
ES (1) ES472672A1 (fr)
IL (1) IL55374A (fr)
IT (1) IT7826808A0 (fr)
PL (1) PL110297B1 (fr)
TR (1) TR19984A (fr)
ZA (1) ZA784700B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0007053A1 (fr) * 1978-07-13 1980-01-23 Bayer Ag Esters d'acides cyclopropyl-2-pyrimidin(4)yl-(thiono)(thiol)phosphoriques(phosphoniques), leur procédé de préparation et leur utilisation comme insecticides et acaricides
EP0023841A2 (fr) * 1979-08-06 1981-02-11 The Dow Chemical Company Esters phosphoreux de 5-pyrimidinols et procédés pour leur préparation, compositions contenant ces esters et leur utilisation comme pesticides

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2831852A1 (de) * 1978-07-20 1980-02-07 Bayer Ag 2-cyclopropyl-pyrimidin(4)yl-(thiono)(thiol)-phosphor-(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
US4426379A (en) 1982-01-27 1984-01-17 Chevron Research Company Insecticidal 2-oxo-3-dialkoxyphosphoro-5-cyclopropyl-1,3,4-oxadiazoline
US4486421A (en) * 1982-11-22 1984-12-04 The Dow Chemical Company Insecticidal phosphorus derivatives of 4-pyrimidinols
US4588711A (en) * 1982-11-22 1986-05-13 The Dow Chemical Company Insecticidal phosphorus derivatives of 6-cycloalkyl-4-pyrimidinols
US4486422A (en) * 1982-11-22 1984-12-04 The Dow Chemical Company Insecticidal phosphorus derivatives of 5-pyrimidinols
US4489068A (en) * 1983-04-28 1984-12-18 The Dow Chemical Company Method and composition for enhancing the insecticidal activity of certain organophosphorus compounds
DE3445465A1 (de) * 1984-12-13 1986-06-19 Bayer Ag, 5090 Leverkusen Pyrimidinyl-thionophosphorsaeureester
JP6604070B2 (ja) * 2015-07-24 2019-11-13 株式会社ジェイテクト 密封装置及びこれを備えた軸受装置

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2754243A (en) * 1951-04-20 1956-07-10 Geigy Ag J R Phosphoric acid esters
DE2209554A1 (de) * 1971-03-04 1972-09-14 Sandoz Ag, Basel (Schweiz) Verfahren zur Herstellung von Phosphor sauree stern
DE2412903A1 (de) * 1973-03-23 1974-09-26 Sandoz Ag Verfahren zur herstellung von phosphorsaeureestern
US4012506A (en) * 1975-07-03 1977-03-15 Ciba-Geigy Corporation Pyrimidyl thio- and dithio-phosphoric acid esters

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2754243A (en) * 1951-04-20 1956-07-10 Geigy Ag J R Phosphoric acid esters
DE2209554A1 (de) * 1971-03-04 1972-09-14 Sandoz Ag, Basel (Schweiz) Verfahren zur Herstellung von Phosphor sauree stern
DE2412903A1 (de) * 1973-03-23 1974-09-26 Sandoz Ag Verfahren zur herstellung von phosphorsaeureestern
US4012506A (en) * 1975-07-03 1977-03-15 Ciba-Geigy Corporation Pyrimidyl thio- and dithio-phosphoric acid esters

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0007053A1 (fr) * 1978-07-13 1980-01-23 Bayer Ag Esters d'acides cyclopropyl-2-pyrimidin(4)yl-(thiono)(thiol)phosphoriques(phosphoniques), leur procédé de préparation et leur utilisation comme insecticides et acaricides
EP0023841A2 (fr) * 1979-08-06 1981-02-11 The Dow Chemical Company Esters phosphoreux de 5-pyrimidinols et procédés pour leur préparation, compositions contenant ces esters et leur utilisation comme pesticides
EP0023841A3 (en) * 1979-08-06 1981-04-29 The Dow Chemical Company 5 pyrimidinols, their phosphorus esters, and methods for their manufacture, compositions containing those esters and their use as pesticides

Also Published As

Publication number Publication date
IL55374A0 (en) 1978-10-31
BR7805355A (pt) 1979-05-02
PL110297B1 (en) 1980-07-31
DK367678A (da) 1979-02-20
AU516426B2 (en) 1981-06-04
DE2860258D1 (en) 1981-01-29
ZA784700B (en) 1979-08-29
EP0000887B1 (fr) 1980-10-29
DD138145A5 (de) 1979-10-17
JPS5441884A (en) 1979-04-03
IL55374A (en) 1982-02-28
IT7826808A0 (it) 1978-08-17
CA1091671A (fr) 1980-12-16
PL209120A1 (pl) 1979-05-21
ES472672A1 (es) 1979-02-16
DE2737401A1 (de) 1979-02-22
TR19984A (tr) 1980-05-09
US4202889A (en) 1980-05-13
CS199216B2 (en) 1980-07-31
AU3905878A (en) 1980-02-21

Similar Documents

Publication Publication Date Title
EP0009566B1 (fr) Esters (thiono)(thiol)-phosphoriques (phosphoniques) de 2-cycloalkyl-pyrimidin(5)yl ou esters de leurs amides, procédé pour leur préparation et leur utilisation comme insecticides, acaricides ou nematicides
EP0128350A2 (fr) Dérivés pyrimidyliques d'acide phosphorique et leur utilisation comme pesticides
EP0000887B1 (fr) Esters et esteramides de pyrimidine-(4) d'acide (thiono)thiol-phosphorique (phosphonique) avec substituant cyclopropyl, leur procédé de préparation et leur application comme insecticides et acaricides
DE2642981C2 (de) Alkoxysubstituierte Pyrimidinyl-thionophosphonsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide
EP0003098A1 (fr) Esters d'acide 2-pyrimidyl-thiono-thiol-phosphorique(phosphonique) substitué par un halogène, procédé pour leur préparation et leur utilisation comme insecticides et acaricides
DE2643262C2 (de) Pyrimidin(5)yl-(thiono)(thiol)-phosphor-(phosphon)-säureester und -esteramide, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide
EP0007501A1 (fr) Esters et esteramides de pyrimidine-(4)yl d'acide (thiono)(thiol)-phosphorique(phosphonique) avec substituant cyclopropyl, procédé pour leur préparation, pesticides, procédé pour leur préparation, leur application et procédé pour combattre les parasites
DE2703712A1 (de) Substituierte pyrimidinon eckige klammer auf (di)-thio eckige klammer zu -phosphor-(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide
EP0007466B1 (fr) Esters 2-cyclopropyl-pyrimidin(4)yliques d'acides thionophosphoniques, procédé pour leur préparation, leur utilisation comme insecticides et acaricides, produits pesticides en contenant et procédé de préparation de ces produits pesticides
CH630094A5 (de) Verfahren zur herstellung von neuen pyrazolopyrimidinyl(thiono)-(thiol)-phosphor(phosphon)-saeureestern.
CH635350A5 (de) Substituierte pyrimidinyl(thio)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide.
CH627346A5 (de) Insektizides und akarizides mittel.
EP0001602A1 (fr) Esters et esteramides substitués d'acides pyrimidinyl-(thiono) (thiol)phosphorique(phosphonique), procédé pour leur préparation et leur application comme insecticides et acaricides
EP0007053B1 (fr) Esters d'acides cyclopropyl-2-pyrimidin(4)yl-(thiono)(thiol)phosphoriques(phosphoniques), leur procédé de préparation et leur utilisation comme insecticides et acaricides
DE2545881C2 (de) 0-Pyrazolopyrimidinthionothiolphosphorsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Bekämpfung von Insekten, Milben und Nematoden
EP0000388B1 (fr) Esters de pyridazinone d'acide (thiono)-phosphorique, leur procédé de préparation et leur application comme insecticides et acaricides
EP0004644A2 (fr) Esters et esteramides d'acides pyrimidin(5)-yle-(thiono)(thiol)-phosphoriques(phosphoniques), leur procédé de préparation et leur utilisation comme insecticides et acaricides
CH631992A5 (de) Verfahren zur herstellung von neuen pyrimidinyl (thiono)(thiol)-phosphor (phosphon)-saeureestern.
CH633805A5 (de) Insektizides und akarizides mittel sowie verfahren zur herstellung neuer alkoxymethyl- bzw. alkylthiomethylsubstituierter pyrazolyl(thiono)(thiol)phosphor(phosphon)-saeureester bzw. -esteramide.
DD148711A5 (de) Schaedlingsbekaempfungsmittel
DE2714038A1 (de) Trifluormethylsulfonylphenylthiono (thiol)phosphorsaeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE2455763A1 (de) O-vinylthiono(thiol)phosphor(phosphon)-saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide
DE2620089A1 (de) Substituierte pyrimidin-bis- eckige klammer auf (thiono)(thiol)-phosphor(phosphon)-saeureester eckige klammer zu, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide
CH633807A5 (de) Carbamoyloxysubstituierte pyrimidinyl(thiono)-(thiol)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide.
DE2627075A1 (de) Substituierte pyridazinyl(thiono)(thiol)-phosphor(phosphon)-saeureesterderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed
AK Designated contracting states

Designated state(s): BE CH DE FR GB NL

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): BE CH DE FR GB NL

REF Corresponds to:

Ref document number: 2860258

Country of ref document: DE

Date of ref document: 19810129

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19820819

Year of fee payment: 5

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19820831

Year of fee payment: 5

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19820930

Year of fee payment: 5

Ref country code: CH

Payment date: 19820930

Year of fee payment: 5

Ref country code: BE

Payment date: 19820930

Year of fee payment: 5

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Effective date: 19830807

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CH

Effective date: 19830831

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19840301

GBPC Gb: european patent ceased through non-payment of renewal fee
NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19840501

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19840502

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19881117

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT