EP0000388B1 - Esters de pyridazinone d'acide (thiono)-phosphorique, leur procédé de préparation et leur application comme insecticides et acaricides - Google Patents

Esters de pyridazinone d'acide (thiono)-phosphorique, leur procédé de préparation et leur application comme insecticides et acaricides Download PDF

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Publication number
EP0000388B1
EP0000388B1 EP78100345A EP78100345A EP0000388B1 EP 0000388 B1 EP0000388 B1 EP 0000388B1 EP 78100345 A EP78100345 A EP 78100345A EP 78100345 A EP78100345 A EP 78100345A EP 0000388 B1 EP0000388 B1 EP 0000388B1
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EP
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Prior art keywords
spp
thiono
butyl
preparation
propyl
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Expired
Application number
EP78100345A
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German (de)
English (en)
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EP0000388A1 (fr
Inventor
Fritz Dr. Maurer
Ingeborg Dr. Hammann
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Bayer AG
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Bayer AG
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Classifications

    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
    • 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
    • C07F9/650905—Six-membered rings having the nitrogen atoms in the positions 1 and 2

Definitions

  • the present invention relates to new pyridazinone (thiono) phosphoric acid esters, a process for their preparation and their use as insecticides and acaricides.
  • O, O-dialkyl-O-pyridazinyl thionophosphoric acid esters e.g. O, O-diethyl-0- (1-phenyl-1,6-di-hydro-pyridaz (6) on (3) yl) -thionophosphoric acid esters are characterized by insecticidal and acaricidal activity (see US Pat. No. 2,759,937).
  • Japanese patent application 74 12 702 0.0-dialkyl-0-3 (N-methyl-6-pyridazinonyl) (thiono) phosphoric acid ester with insecticidal properties is known.
  • the pyridazinone (thiono) phosphoric acid esters mentioned at the beginning and described in more detail below are, as shown by comparative experiments, unexpectedly superior to the known structurally similar phosphoric acid esters as insecticides and acaricides.
  • the pyridazinone (thiono) phosphoric acid esters (I) according to the invention have better insecticidal and acaricidal activity than the previously known compounds of analogous constitution and the same direction of action.
  • the products according to the present invention thus represent a real enrichment of the technology.
  • the 1,6-dihydro-3-hydroxy-1-iso-propyl-pyridazin (6) on (III) which is also to be used as the starting material can also be prepared by processes known from the literature.
  • 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 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, chlorobenzene, or ether, e.g. Diethyl
  • 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 trimethylamine, triethylamine, dimethylaniline, dimethylbenzylamine and pyridine, have proven particularly useful.
  • the reaction temperature can be varied within a wide range. 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 components are preferably used in equivalent ratios.
  • An excess of one or the other component has no significant advantages.
  • the reaction components are generally combined in one of the specified solvents and are usually stirred at elevated temperature for one or more hours to complete the reaction. Then an organic solvent is added, e.g. Toiuol, and works up the organic phase as usual by washing, drying and distilling off the solvent.
  • the new compounds are 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.
  • the pyridazinone (thiono) phosphoric acid esters according to the invention are notable for excellent insecticidal and acaricidal activity. They act not only against plant, hygiene and storage pests, but also in the veterinary medical sector against animal parasites (ectoparasites), such as parasitic fly larvae. With low phytoxicity, the compounds have both a good action against sucking and eating 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.
  • 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 mist 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.,
  • 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, 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, 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, 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.
  • 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 paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and the like 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 those 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 powders, such as
  • 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.
  • 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 plants (Brassica oleracea), which are heavily infested with peach aphids (Myzus persicae), are sprayed to runoff point with the active substance preparation.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • 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.
  • 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%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
  • the 1-isopropyl-1,6-dihydro-3-hydroxy-6-oxopyridazine to be used as the starting material can be prepared, for example, as follows:

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (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)

Claims (6)

1. Composés de formule
Figure imgb0015
dans laquelle
R et R' représentent chacun un alcoyle identique ou différent et
X représente de l'oxygène ou du soufre.
2. Procédé de préparation de composés selon la revendication 1, caractérisé en ce qu'on fait réagir des halogénures de diesters d'acide (thiono)phosphorique de formule:
Figure imgb0016
dans laquelle
R, R' et X ont la signification indiquée à la revendication 1 et Hal repréesente de l'halogène, de préférence du chlore,
avec de la 1,6-dihydro-3-hydroxy-1-isopropyl-pyridazin(6)one de formule:
Figure imgb0017
éventuèllement sous forme de sels alcalins, alcalino-terreux ou ammoniacaux ou éventuellement en présence d'un accepteur d'acide et éventuellement en présence d'un solvant.
3. Agent insecticide et acaricide, caractérisé par une teneur en au moins un composé selon la revendication 1.
4. Procédé pour combattre les insectes et les arachnides, caractérisé en ce qu'on fait agir des composés selon la revendication 1 sur des insectes et des arachnides ou sur leur espace vital.
5. Utilisation des composés selon la revendication 1 pour combattre les insectes et les arachnides.
6. Procédé de préparation de composés insecticides et açaricides, caractérisé en ce qu'on mélange des composés selon la revendication 1 avec des diluants et/ou des agents tensioactifs.
EP78100345A 1977-07-15 1978-07-11 Esters de pyridazinone d'acide (thiono)-phosphorique, leur procédé de préparation et leur application comme insecticides et acaricides Expired EP0000388B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772732101 DE2732101A1 (de) 1977-07-15 1977-07-15 Pyridazinon(thiono)-phosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE2732101 1977-07-15

Publications (2)

Publication Number Publication Date
EP0000388A1 EP0000388A1 (fr) 1979-01-24
EP0000388B1 true EP0000388B1 (fr) 1980-11-26

Family

ID=6014045

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EP78100345A Expired EP0000388B1 (fr) 1977-07-15 1978-07-11 Esters de pyridazinone d'acide (thiono)-phosphorique, leur procédé de préparation et leur application comme insecticides et acaricides

Country Status (19)

Country Link
US (1) US4219546A (fr)
EP (1) EP0000388B1 (fr)
JP (1) JPS5419988A (fr)
AR (1) AR218924A1 (fr)
AT (1) AT354812B (fr)
AU (1) AU514922B2 (fr)
BR (1) BR7804540A (fr)
CA (1) CA1099270A (fr)
CS (1) CS207631B2 (fr)
DE (2) DE2732101A1 (fr)
DK (1) DK318478A (fr)
EG (1) EG13407A (fr)
ES (1) ES471749A1 (fr)
IL (1) IL55123A (fr)
IT (1) IT7825663A0 (fr)
NZ (1) NZ187841A (fr)
PT (1) PT68271A (fr)
TR (1) TR19756A (fr)
ZA (1) ZA784027B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4571397A (en) * 1982-03-05 1986-02-18 Nissan Chemical Industries Pyridazinone derivatives, preparation thereof, and agricultural and horticultural fungicidal, insecticidal, acaricidal, nematicidal compositions containing said derivatives
JPH0350221U (fr) * 1989-09-22 1991-05-16

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL93954C (fr) * 1955-03-21 1900-01-01
US3100206A (en) * 1961-05-05 1963-08-06 Dow Chemical Co O-(1,6-dihydro-6-oxo - 3 - pyridazinyl) o - alkyl phosphoramidate and phosphoramidothioate
CH507304A (de) * 1968-03-27 1971-05-15 Bayer Ag Verfahren zur Herstellung von Thionophosphonsäureestern
JPS4912702B1 (fr) * 1970-09-11 1974-03-26
DE2343741A1 (de) * 1973-08-30 1975-03-20 Bayer Ag 0-aethyl-s-0- eckige klammer auf pyridaz-(3)-on-(6)-yl eckige klammer zu -thionothiolphosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE2531340A1 (de) * 1975-07-12 1977-01-27 Bayer Ag O-aethyl-o-pyridazinylthionobenzolphosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE2603993A1 (de) * 1976-02-03 1977-08-04 Bayer Ag (thiono)(thiol)pyridazinphosphor (phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide

Also Published As

Publication number Publication date
ZA784027B (en) 1979-07-25
ATA510578A (de) 1979-06-15
PT68271A (de) 1978-08-01
JPS5419988A (en) 1979-02-15
NZ187841A (en) 1980-04-28
EP0000388A1 (fr) 1979-01-24
TR19756A (tr) 1979-11-30
DK318478A (da) 1979-01-16
US4219546A (en) 1980-08-26
DE2732101A1 (de) 1979-01-25
BR7804540A (pt) 1979-03-06
IL55123A0 (en) 1978-09-29
CA1099270A (fr) 1981-04-14
CS207631B2 (en) 1981-08-31
AR218924A1 (es) 1980-07-15
DE2860340D1 (en) 1981-02-12
ES471749A1 (es) 1979-02-01
AU514922B2 (en) 1981-03-05
EG13407A (en) 1982-03-31
AU3795978A (en) 1980-01-17
AT354812B (de) 1979-01-25
IL55123A (en) 1982-05-31
IT7825663A0 (it) 1978-07-13

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