EP0000888A1 - N-(aminométhylène)-(mono ou dithio) diester amides de l'acide phosphorique, leur procédé de préparation et leur application comme insecticides, acaricides et nématocides - Google Patents

N-(aminométhylène)-(mono ou dithio) diester amides de l'acide phosphorique, leur procédé de préparation et leur application comme insecticides, acaricides et nématocides Download PDF

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Publication number
EP0000888A1
EP0000888A1 EP78100600A EP78100600A EP0000888A1 EP 0000888 A1 EP0000888 A1 EP 0000888A1 EP 78100600 A EP78100600 A EP 78100600A EP 78100600 A EP78100600 A EP 78100600A EP 0000888 A1 EP0000888 A1 EP 0000888A1
Authority
EP
European Patent Office
Prior art keywords
spp
dithio
mono
aminomethylene
phosphoric
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.)
Withdrawn
Application number
EP78100600A
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German (de)
English (en)
Inventor
Hellmut Dr. Hoffmann
Ingeborg Dr. Hammann
Bernhard Dr. Homeyer
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 EP0000888A1 publication Critical patent/EP0000888A1/fr
Withdrawn legal-status Critical Current

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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
    • A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
    • A01N57/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing acyclic or cycloaliphatic 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines

Definitions

  • the present invention relates to new N- (aminomethylene) - (mono- or dithio) -phosphoric diester amides, a process for their preparation and their use as insecticides, acaricides and nematicides.
  • O S-dialkylthiolphosphoric acid di-ester amides
  • O S-dimethyl-N- (methyl or tert-butyl aminomethylene) thiolphosphoric diester amide
  • insecticidal and acaricidal properties see German Offenlegungsschrift 2 211 338.
  • N- (aminomethylene) - (mono- or dithio) -phosphoric diester amides (I) are obtained if N- (monoalkylaminomethylene) - (mono- or dithio) -phosphoric acid diesteramides of the formula in which R, R 1 , R 2 and X have the meaning given above, optionally reacted with acetic anhydride in the presence of an organic solvent.
  • the N- (aminomethylene) - (mono- or, dithio) -phosphoric diester amides according to the invention have better insecticidal, acaricidal and nematicidal activity than the compounds of analogous constitution and the same direction of action known from the literature.
  • the fabrics according to the present invention thus represent a real enrichment of technology.
  • N- (aminomethylene) - (mono- or dithio) -phosphoric acid esteramides to be used as starting materials are known (cf. German Offenlegungsschrift 2 211 338) or can be prepared from the corresponding known N- (alkoxymethylene) - (mono- or . dithio) -phosphoric diester amides (see German Offenlegungsschrift 2,517 lol) be produced with monoalkylamines.
  • Examples include: O, S-dimethyl-, O, S-diethyl-, O, S-di-n-propyl-, O, S-di-iso-propyl-, 0-methyl-S- ethyl, 0-methyl-Sn-propyl, 0-methyl-S-iso-propyl, 0-methyl-Sn-butyl, 0-methyl-S-iso-butyl, O-methyl-S-sec .-Butyl-, O-methyl-S-tert.-butyl-, O-ethyl-Sn-propyl-, 0-ethyl-S-iso-propyl-, O-ethyl-Sn-butyl-, O-ethyl- S-iso-butyl-, O-ethyl-S-sec-butyl-, O-ethyl-S-tert.-butyl-, 0-n-propyl-S-ethyl-
  • the acetic anhydride to be used as a starting material is known and can also be easily produced on an industrial scale.
  • the process for the preparation of the compounds according to the invention is preferably carried out in acetic anhydride, which functions as a reactive component and at the same time as a solvent.
  • the reaction temperature can be varied within a wide range. In general, one works between 40 and 100 ° C, preferably at 55 to 75 ° C.
  • the reaction is generally allowed to proceed at normal pressure.
  • the acetic anhydride is used in excess and the mixture of the phosphoric ester amide and acetic anhydride is heated for several hours. Thereafter the reaction mixture is dissolved in an organic solvent, e.g. Toluene, dissolved. The organic phase is washed with water to remove the resulting acetic acid and then with a bicarbonate solution. The solvent is removed in vacuo.
  • an organic solvent e.g. Toluene
  • the new compounds are obtained in the form of oils, some of which 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.
  • Trichoplusia ni Carpocapaa pomonella, Pieris spp., Chilo app., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clyaia ambiguella, Homona magnanima, Tortrix viranana. From the order of the Coleoptera z. B.
  • Diprion spp. Hoplocampa spp., Lasius spp., Monomorium pharaonia, Veapa app. From the order of the Diptera e.g. A ⁇ des spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus app., Hyppobosca spp., Stomoxya spp.
  • a ⁇ des spp. Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus app
  • Oestrus spp. Hypoderma spp., Tabanus sop., Tannia spp., Bibio hortulanua, Oscinella frit, Phorbia sop., Pegomyia hyoscyami, Ceratitia capitata, Dacus oleae, Tipula paludosa.
  • Siphonaptera e.g. Xenopsylla cheopis
  • Ceratophyllus spp . From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans.
  • Acarina e.g. Acarus siro, Argas spp.
  • Ornithodoros spp. Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus sp p. , Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
  • Plant parasitic nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus 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 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.
  • These formulations are prepared in a known manner, e.g.
  • 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 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 kaolin, clay
  • 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 ingredients are also suitable for controlling pests in the veterinary sector.
  • 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%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae 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.
  • Test insect Phaedon cochleariae larvae
  • 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, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the active ingredient preparation is intimately mixed with the soil.
  • the treated soil is filled into pots and planted with cabbage (Brassica oleracea).
  • the active ingredient can be taken up from the soil by the plant roots and transported to the leaves.
  • the root systemic effect of the active ingredient is derived from the number of killings. It is 100% when all test animals have been killed and 0% when as many test insects are still alive as in the untreated control.
  • Test nematode Meloidogyne incognita
  • 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, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the active ingredient preparation is intimately mixed with soil that is heavily contaminated with the test nematodes.
  • concentration of the active ingredient in the preparation is practically irrelevant, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm.
  • the treated soil is filled into pots, lettuce is sown and the pots are kept at a greenhouse temperature of 27 ° C.
  • the lettuce roots are examined for nematode infestation (root galls) and the effectiveness of the active ingredient is determined in%.
  • the efficiency is 100% if the infestation is completely avoided, it is 0% if the infestation is as high as that of the control plants in untreated, but equally contaminated soil.
  • a mixture of 27 g (0.1 mol) of O-ethyl-Sn-propyl-N- (isopropylaminomethylene) dithiophosphoric diester amide and 12 g of acetic anhydride is heated to 70 ° C. for 6 hours with stirring.
  • the reaction mixture is dissolved in 300 ml of toluene, washed twice with water and once with a bicarbonate solution. The solvent is removed in vacuo and the residue is distilled on the mercury pump.
  • N- (monoalkylamino-methylene) - (mono- or dithio) -phosphoric diester amides (II) to be used as starting materials can be prepared as described below: In the well-stirred and cooled mixture of 7oo al acetonitrile and loo g 7o% aqueous isopropylamine solution, drop 256 g (1 mol) of O-ethyl at -5 to 0 ° C within 1 hour.

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  • 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)
EP78100600A 1977-08-19 1978-08-07 N-(aminométhylène)-(mono ou dithio) diester amides de l'acide phosphorique, leur procédé de préparation et leur application comme insecticides, acaricides et nématocides Withdrawn EP0000888A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772737403 DE2737403A1 (de) 1977-08-19 1977-08-19 N-(aminomethylen)-(mono- bzw. dithio) -phosphorsaeurediesteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide
DE2737403 1977-08-19

Publications (1)

Publication Number Publication Date
EP0000888A1 true EP0000888A1 (fr) 1979-03-07

Family

ID=6016782

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100600A Withdrawn EP0000888A1 (fr) 1977-08-19 1978-08-07 N-(aminométhylène)-(mono ou dithio) diester amides de l'acide phosphorique, leur procédé de préparation et leur application comme insecticides, acaricides et nématocides

Country Status (14)

Country Link
US (1) US4176181A (fr)
EP (1) EP0000888A1 (fr)
JP (2) JPS5441823A (fr)
AU (1) AU3905978A (fr)
BR (1) BR7805332A (fr)
CS (1) CS199217B2 (fr)
DD (1) DD138271A5 (fr)
DE (1) DE2737403A1 (fr)
DK (1) DK367178A (fr)
ES (1) ES472670A1 (fr)
IL (1) IL55380A0 (fr)
IT (1) IT7826801A0 (fr)
PL (1) PL110572B1 (fr)
ZA (1) ZA784698B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2568966A1 (fr) * 1984-07-04 1986-02-14 Archetti Snc Luigi Archetti C Systeme de construction de poulies composees en tole emboutie comprenant plusieurs poulies modulaires et poulie obtenue

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2831934A1 (de) * 1978-07-20 1980-02-07 Bayer Ag O-aethyl-s-n-propyl-n-aminomethyliden-thiolphosphorsaeurediesterimide, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
JPS60178733U (ja) * 1984-05-04 1985-11-27 榎本　正実 ユニツトバス用自動換気装置
CN105131033B (zh) * 2015-08-10 2017-05-31 河北工业大学 N‑(1,2‑二苯基‑2‑氨基)‑硫代磷酰胺盐及其应用

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH540646A (de) * 1969-12-15 1973-08-31 Stauffer Chemical Co Biocides Mittel
DE2211338A1 (de) * 1972-03-09 1973-09-13 Bayer Ag N-(aminomethyliden)-thiol-phosphorsaeureesterimide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE2312738A1 (de) * 1972-03-17 1973-09-20 Ciba Geigy Ag Neue kondensationsprodukte
DE2216552A1 (de) * 1972-04-06 1973-10-11 Bayer Ag Disubstituierte n- eckige klammer auf aminomethyliden eckige klammer zu -thiol (thiono)-phosphorsaeureesterimide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DD106256A5 (fr) * 1971-12-17 1974-06-12
DE2420069A1 (de) * 1974-04-25 1975-11-13 Bayer Ag N,n-dimethyl-n'- eckige klammer auf 0-phenyl(thiono)-alkanphosphonyl eckige klammer zu formamidine, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3826830A (en) * 1971-01-11 1974-07-30 Stauffer Chemical Co Certain phosphorus containing amidine compounds as insecticides and acaricides

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH540646A (de) * 1969-12-15 1973-08-31 Stauffer Chemical Co Biocides Mittel
DD106256A5 (fr) * 1971-12-17 1974-06-12
DE2211338A1 (de) * 1972-03-09 1973-09-13 Bayer Ag N-(aminomethyliden)-thiol-phosphorsaeureesterimide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE2312738A1 (de) * 1972-03-17 1973-09-20 Ciba Geigy Ag Neue kondensationsprodukte
DE2216552A1 (de) * 1972-04-06 1973-10-11 Bayer Ag Disubstituierte n- eckige klammer auf aminomethyliden eckige klammer zu -thiol (thiono)-phosphorsaeureesterimide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE2420069A1 (de) * 1974-04-25 1975-11-13 Bayer Ag N,n-dimethyl-n'- eckige klammer auf 0-phenyl(thiono)-alkanphosphonyl eckige klammer zu formamidine, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2568966A1 (fr) * 1984-07-04 1986-02-14 Archetti Snc Luigi Archetti C Systeme de construction de poulies composees en tole emboutie comprenant plusieurs poulies modulaires et poulie obtenue

Also Published As

Publication number Publication date
DE2737403A1 (de) 1979-02-22
DD138271A5 (de) 1979-10-24
BR7805332A (pt) 1979-05-02
JPS5441823A (en) 1979-04-03
AU3905978A (en) 1980-02-21
PL209093A1 (pl) 1979-05-21
IT7826801A0 (it) 1978-08-17
ES472670A1 (es) 1979-02-16
US4176181A (en) 1979-11-27
PL110572B1 (en) 1980-07-31
CS199217B2 (en) 1980-07-31
DK367178A (da) 1979-02-20
JPS5441824A (en) 1979-04-03
ZA784698B (en) 1979-08-29
IL55380A0 (en) 1978-10-31

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Inventor name: HAMMANN, INGEBORG, DR.