CH480799A - Pesticides - Google Patents

Pesticides

Info

Publication number
CH480799A
CH480799A CH37867A CH37867A CH480799A CH 480799 A CH480799 A CH 480799A CH 37867 A CH37867 A CH 37867A CH 37867 A CH37867 A CH 37867A CH 480799 A CH480799 A CH 480799A
Authority
CH
Switzerland
Prior art keywords
pesticides
agents
dimethyl
active ingredient
insecticidal
Prior art date
Application number
CH37867A
Other languages
German (de)
Inventor
Eberhard Dipl Chem Marx
Original Assignee
Wolfen Filmfab Veb
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 Wolfen Filmfab Veb filed Critical Wolfen Filmfab Veb
Publication of CH480799A publication Critical patent/CH480799A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/16Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165Esters of thiophosphoric acids
    • C07F9/1651Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

  

  



  Schädlingsbekämpfungsmittel
Die Herstellung von   ss-Alkylmercaptoäthyl-thiophos-    phorsäureestern sowie die Verwendung dieser Verbindungen als Wirkstoff für Schädlingsbekämpfungsmittel ist bekannt (DBP 836 349, DBP 850677, DBP 935 432). Diese bekannten Mittel besitzen eine ausgezeichnete kontaktinsektizide und innertherapeutische insektizide Wirkung. Bei längerer Anwendung derartiger Mittel erfolgt jedoch - wie allgemein bekannt - eine Gewöhnung der Schädlinge an die Bekämpfungsmittel, so dass diese allmählich ihre Wirksamkeit verlieren und durch andere wirksamere Mittel ersetzt werden müssen.



   Zweck und Aufgabe der vorliegenden Erfindung war es nun, neue Schädlingsbekämpfungsmittel zu finden, deren Wirkstoffe bei einer mit den obengenannten Wirkstoffen gleichwertigen Wirksamkeit eine von diesen abweichende Struktur besitzen.



   Es wurde gefunden, dass Schädlingsbekämpfungsmittel, die als aktive Komponente einen ss-Alkoxy äthylmercapto-)alkyl-thiophosphorsäure-dialkylester der Formel
EMI1.1     
 in der R1, R2,   Rg    für niedere Alkylreste steht, enthalten, den geforderten Bedingungen entsprechen und eine ausgezeichnete insektizide und akarizide Wirkung besitzen.



   Diese bisher noch nicht beschriebenen Verbindungen können nach den allgemein bekannten Herstellungsverfahren, beispielsweise durch Umsetzug von Verbindungen der Formel    HOC, H4SC2H4OR    mit Dialkylchlorthiophosphaten in Gegenwart säurebindender Mittel, erhalten werden.



   Beispiel I
In eine Lösung von 90 g   ss-Oxy-ss'-oxyäthyl- diäthyl-    sulfid in 150 ml Benzol werden 80 g getrocknetes, feingepulvertes Kaliumcarbonat eingetragen. Man tropft unter Rühren innerhalb 30 Minuten bei   35  C    80 g Dimethylchlorthiophosphat zu und rührt weitere 8 Stunden bei der gleichen Temperatur. Danach wird abgesaugt, 3mal mit je 25 ml Benzol gewaschen, die benzolische Lösung mit Wasser gewaschen, über Natriumsulfat getrocknet und das Lösungsmittel abdestilliert.



   Bei einem Vakuum von 5 Torr und einer Badtemperatur von 90 bis 95   OC    verbleiben als   Destillationsrück-    stand 118 g   0,0-Dimethyl-0,2-fl'-äthoxy-äthylmercap-    to)-äthylthiophosphat in Form eines schwach gelblich gefärbten, wasserunlöslichen   ÖIs.    Die Ausbeute beträgt 86   O/o    der Theorie.



   Beispiel 2
Die insektizide Prüfung des   0, 0-Dimethyl-0,2-(K-    äthoxy-äthylmercapto)-äthylthiophosphats erfolgte an Fliegen (Musca domestica), an Kornkäfern (Sitophilus granarius) und Blattläusen (Aoyrthosiphon pisum, Aphis fabae) in Äther gelöst (Angabe der Wirkstoffmenge in   1ig/cm2),    an Reismehlkäferlarven (Tribolium confusum) als Wirkstoff im Weizenmehl (Angabe der prozentualen Wirkstoffmenge im Mehl).



   Der Wirkungsgrad wurde an Kornkäfern und Fliegen nach achtzehnstündiger, an Blattläsuen nach sechsstündiger und an Reismehlkäferlarven nach zehntägiger Expositionszeit bestimmt.



  Anwendung gegen Wirkstoffmenge Wirkungsgrad in   g/cm2    bzw.0/o in   O/o    M. domestica 1,25 45
12,50 100 S. granarius 13 80
130 100 A. pisum 10 60
100 100 A. fabae 100 100 T. confusum 0,01 60
0,025 100
Beispiel 3
Mit Spinnmilben (Tetranychus articae) infizierte Phaseolus-Bohnen wurden mit einer 0,2   0/obigen    Lösung eines Präparates behandelt, das 25   O/o      0,0-Dimethyl-0,2-    (ss-äthoxy-äthylmercapto)-äthylthiophosphat, 25   O/o    Aceton und 50   O/o    eines oxäthylierten Alkylphenols enthielt.



  Bei der Kontrolle nach 3 Tagen konnte ein nahezu hundertprozentiger Bekämpfungserfolg festgestellt werden.



  



  Pesticides
The preparation of β-alkyl mercaptoethyl thiophosphoric acid esters and the use of these compounds as active ingredients for pesticides is known (DBP 836 349, DBP 850677, DBP 935 432). These known agents have an excellent contact insecticidal and intra-therapeutic insecticidal effect. If such agents are used for a long time, however, as is generally known, the pests get used to the control agents, so that they gradually lose their effectiveness and have to be replaced by other more effective agents.



   It was the purpose and object of the present invention to find new pesticides whose active ingredients have a structure that differs from the above-mentioned active ingredients while being effective.



   It has been found that pesticides which have an s-alkoxy äthylmercapto-) alkyl-thiophosphoric acid dialkyl ester of the formula
EMI1.1
 in which R1, R2, Rg stands for lower alkyl radicals, correspond to the required conditions and have an excellent insecticidal and acaricidal effect.



   These hitherto not yet described compounds can be obtained by the generally known production processes, for example by reacting compounds of the formula HOC, H4SC2H4OR with dialkyl chlorothiophosphates in the presence of acid-binding agents.



   Example I.
80 g of dried, finely powdered potassium carbonate are added to a solution of 90 g of ss-oxy-ss'-oxyethyl diethyl sulfide in 150 ml of benzene. 80 g of dimethyl chlorothiophosphate are added dropwise with stirring at 35 ° C. over the course of 30 minutes, and the mixture is stirred for a further 8 hours at the same temperature. It is then filtered off with suction, washed 3 times with 25 ml of benzene each time, the benzene solution is washed with water and dried over sodium sulfate and the solvent is distilled off.



   At a vacuum of 5 torr and a bath temperature of 90 to 95 ° C., 118 g of 0,0-dimethyl-0,2-fl'-ethoxyethyl mercapto) ethyl thiophosphate remain as distillation residue in the form of a pale yellowish, water-insoluble one Oil. The yield is 86% of theory.



   Example 2
The insecticidal test of 0, 0-dimethyl-0,2- (K-ethoxy-äthylmercapto) -äthylthiophosphats was carried out on flies (Musca domestica), on grain beetles (Sitophilus granarius) and aphids (Aoyrthosiphon pisum, Aphis fabae) dissolved in ether ( Specification of the amount of active ingredient in 1ig / cm2), on rice flour beetle larvae (Tribolium confusum) as the active ingredient in wheat flour (information on the percentage of active ingredient in the flour).



   The degree of effectiveness was determined on grain weevils and flies after eighteen hours of exposure, on leaf lice after six hours and on rice flour beetle larvae after ten days of exposure.



  Use against the amount of active ingredient, efficiency in g / cm2 or 0 / o in O / o M. domestica 1.25 45
12.50 100 S. granarius 13 80
130 100 A. pisum 10 60
100 100 A. fabae 100 100 T. confusum 0.01 60
0.025 100
Example 3
Phaseolus beans infected with spider mites (Tetranychus articae) were treated with a 0.2% above solution of a preparation containing 25% of 0.0-dimethyl-0.2- (ss-ethoxy-ethylmercapto) -ethylthiophosphate, 25% O / o acetone and 50 O / o of an oxethylated alkylphenol.



  When checking after 3 days, an almost 100% control success could be determined.

 

Claims (1)

PATENTANSPRUCH Schädlingsbekämpfungsmittel, dadurch gekennzeichnet, dass es als aktive Komponente einen (ss-Alkoxy äthylmercapto)-alkylthiophosphorsäure-dialkylester der Formel EMI2.1 enthält, in der R1, R2, R8 für niedere Alkylreste stehen. PATENT CLAIM Pesticides, characterized in that the active component is an (β-alkoxy äthylmercapto) -alkylthiophosphoric acid dialkyl ester of the formula EMI2.1 contains, in which R1, R2, R8 represent lower alkyl radicals.
CH37867A 1966-07-26 1967-01-11 Pesticides CH480799A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DD11897166 1966-07-26

Publications (1)

Publication Number Publication Date
CH480799A true CH480799A (en) 1969-11-15

Family

ID=5478998

Family Applications (1)

Application Number Title Priority Date Filing Date
CH37867A CH480799A (en) 1966-07-26 1967-01-11 Pesticides

Country Status (1)

Country Link
CH (1) CH480799A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0215570A1 (en) * 1985-08-13 1987-03-25 Hironori Kushibiki Organo phosporic acid dithioester insecticides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0215570A1 (en) * 1985-08-13 1987-03-25 Hironori Kushibiki Organo phosporic acid dithioester insecticides

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