EP0000887B1 - Cyclopropylsubstituierte Pyrimidin(4)yl(thiono)-(thiol)-phosphor(phosphon)-säureester bzw. -esteramide, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide - Google Patents

Cyclopropylsubstituierte Pyrimidin(4)yl(thiono)-(thiol)-phosphor(phosphon)-säureester bzw. -esteramide, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide Download PDF

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Publication number
EP0000887B1
EP0000887B1 EP78100599A EP78100599A EP0000887B1 EP 0000887 B1 EP0000887 B1 EP 0000887B1 EP 78100599 A EP78100599 A EP 78100599A EP 78100599 A EP78100599 A EP 78100599A EP 0000887 B1 EP0000887 B1 EP 0000887B1
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EP
European Patent Office
Prior art keywords
spp
cyclopropyl
iso
propyl
ethyl
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.)
Expired
Application number
EP78100599A
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German (de)
English (en)
French (fr)
Other versions
EP0000887A1 (de
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
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0000887A1 publication Critical patent/EP0000887A1/de
Application granted granted Critical
Publication of EP0000887B1 publication Critical patent/EP0000887B1/de
Expired legal-status Critical Current

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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.
  • O, O-dialkyl-O-pyrimidinylthionophosphoric acid esters e.g. O, O-dimethyl-0- [2-ethyl-4-ethoxypyrimidine (6) yl] - or O, O-diethyl-O- [2-isopropyl-4-methyl-pyrimidine (6) yl] thionophosphoric acid ester
  • O, O-dialkyl-O-pyrimidinylthionophosphoric acid esters e.g. O, O-dimethyl-0- [2-ethyl-4-ethoxypyrimidine (6) yl] - or O, O-diethyl-O- [2-isopropyl-4-methyl-pyrimidine (6) yl] thionophosphoric acid ester
  • US Pat. No. 4,012,506 discloses cyclopropyl-substituted pyrimidine- (4) -yl-thio- and dithiophosphoric acid esters with insecticidal and acaricidal activity.
  • these active compounds are inferior to the compounds according to the invention in their insecticidal and acaricidal activity.
  • the cyclopropyl-substituted pyrimidine (4) yl (thiono) (thiol) -phosphorus (phosphonic) acid esters or ester amides have a better insecticidal and acaricidal activity than the known pyrimidine (6) yl-thionophosphoric acid esters of analogous constitution and the same direction of action.
  • the compounds of the present invention thus represent a real enrichment of technology.
  • the (thiono) (thiol) phosphorus (phosphonic) acid ester or ester amide halides (II) to be used as starting materials are known and can also be prepared industrially by processes known from the literature. Examples include: O, O-dimethyl, O, O-diethyl, 0.0-di-n-propyl, O, O-di-iso-propyl, O, O-di- n-butyl-, O, O-di-iso-butyl-, O, O-Di-sek, -butyl-, O-Methyl-O-ethyl-, O-Methyl-On-propyl-, O-Methyl- O-iso-propyl-, O-methyl-on-butyl-, O-methyl-O-iso-butyl-, O-methyl-O-sec-butyl-, O-ethyl-on-propyl-, 0- Ethyl-
  • the 2-cyclopropyl-4-hydroxy-pyrimidines (III) which are also 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. Diethyl and dibutyl ether, dioxane, also ketones, for example acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone, and also nitriles, such as aceto and propionitrile.
  • chlorinated hydrocarbons such as benzene, toluene, xylene, gasoline, methylene chloride, chloroform, carbon tetrachloride, chlor
  • All customary acid binders can be used as acid acceptors.
  • Alkali carbonates and alcoholates such as sodium and potassium carbonate, methylate or ethylate, and also aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine and pyridine, have proven particularly useful.
  • the reaction temperature can be varied within a wide range. in the generally one works between 0 and 100 ° C, preferably at 20 to 60 ° 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 can usually not 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 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 powders, active ingredient-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 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 powders, active ingredient-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 smoking cartridges, cans, spirals, etc. as well as
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate 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.
  • water e.g. organic solvents can also be used as auxiliary 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 paraffins, e.g.
  • Petroleum fractions oil 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 pressure, e.g.
  • Aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; as solid carriers: natural rock flour, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates; So solid carriers for granules: 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 material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents: nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
  • 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 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.
  • 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).
  • 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.
  • 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 the preparation of active compound.
  • 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.
  • the condition of the test animals is checked 3 days after starting the experiments.
  • the death rate is determined in%.
  • 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 be prepared, for example, as follows:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • 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 Cyclopropylsubstituierte Pyrimidin(4)yl(thiono)-(thiol)-phosphor(phosphon)-säureester bzw. -esteramide, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide Expired EP0000887B1 (de)

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 EP0000887A1 (de) 1979-03-07
EP0000887B1 true EP0000887B1 (de) 1980-10-29

Family

ID=6016780

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100599A Expired EP0000887B1 (de) 1977-08-19 1978-08-07 Cyclopropylsubstituierte Pyrimidin(4)yl(thiono)-(thiol)-phosphor(phosphon)-säureester bzw. -esteramide, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide

Country Status (16)

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

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2830766A1 (de) * 1978-07-13 1980-01-31 Bayer Ag 2-cyclopropyl-pyrimidin(4)yl-(thiono) (thiol)-phosphor-(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
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
NZ194555A (en) * 1979-08-06 1983-07-29 Dow Chemical Co Alkylcycloalkyl-5-pyrimidinols phosphorus derivatives pesticidal compositions
US4426379A (en) 1982-01-27 1984-01-17 Chevron Research Company Insecticidal 2-oxo-3-dialkoxyphosphoro-5-cyclopropyl-1,3,4-oxadiazoline
US4486422A (en) * 1982-11-22 1984-12-04 The Dow Chemical Company Insecticidal phosphorus derivatives of 5-pyrimidinols
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
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

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA529113A (en) * 1951-04-20 1956-08-14 J. R. Geigy A.-G. Phosphoric acid esters
DK130683B (da) * 1971-03-04 1975-03-24 Sandoz Ag Pesticidt virksomme pyrimidinylphosphorsyreestere.
ZA741376B (en) * 1973-03-23 1975-10-29 Sandoz Ltd Improvements in or relating to organic compounds
US4012506A (en) * 1975-07-03 1977-03-15 Ciba-Geigy Corporation Pyrimidyl thio- and dithio-phosphoric acid esters

Also Published As

Publication number Publication date
CS199216B2 (en) 1980-07-31
CA1091671A (en) 1980-12-16
IT7826808A0 (it) 1978-08-17
EP0000887A1 (de) 1979-03-07
AU516426B2 (en) 1981-06-04
IL55374A0 (en) 1978-10-31
DK367678A (da) 1979-02-20
ES472672A1 (es) 1979-02-16
DD138145A5 (de) 1979-10-17
IL55374A (en) 1982-02-28
DE2860258D1 (en) 1981-01-29
TR19984A (tr) 1980-05-09
PL209120A1 (pl) 1979-05-21
AU3905878A (en) 1980-02-21
PL110297B1 (en) 1980-07-31
JPS5441884A (en) 1979-04-03
BR7805355A (pt) 1979-05-02
ZA784700B (en) 1979-08-29
US4202889A (en) 1980-05-13
DE2737401A1 (de) 1979-02-22

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