DE1173723B - Preparations for the control of insects - Google Patents

Preparations for the control of insects

Info

Publication number
DE1173723B
DE1173723B DEB59454A DEB0059454A DE1173723B DE 1173723 B DE1173723 B DE 1173723B DE B59454 A DEB59454 A DE B59454A DE B0059454 A DEB0059454 A DE B0059454A DE 1173723 B DE1173723 B DE 1173723B
Authority
DE
Germany
Prior art keywords
insects
preparations
control
compounds
active ingredients
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.)
Pending
Application number
DEB59454A
Other languages
German (de)
Inventor
Dr Heinz Pohlemann
Dr Siegfried Winderl
Dr Herbert Stummeyer
Dr Heinrich Adolphi
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DEB59454A priority Critical patent/DE1173723B/en
Publication of DE1173723B publication Critical patent/DE1173723B/en
Pending legal-status Critical Current

Links

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
    • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur 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 System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/173—Esters of thiophosphoric acids with unsaturated acyclic alcohols

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)

Description

Mittel zur Bekämpfung von Insekten Es ist bekannt, O,O-Dialkylthionophosphorsäureester von in 1-Stellung substituierten Butenolen (deutsche Patentschrift 1 072 616) oder O,O-Dialkylthiolphosphorsäureester von verzweigten, durch Halogen substituierten und eine Sulfongruppe enthaltenden Alkoholen (deutsche Auslegeschrift 1 04Ç 939) oder O,O-Dialkylthiophosphorsäureester von Butenolen (deutsche Patentschrift 1 058 044) zur Bekämpfung von Insekten zu verwenden. Die Wirkung der Verbindungen befriedigt jedoch nicht.Means for controlling insects It is known, O, O-dialkylthionophosphoric acid ester of butenols substituted in the 1-position (German Patent 1,072,616) or O, O-dialkylthiol phosphoric acid esters of branched, halogen-substituted and alcohols containing a sulfonic group (German Auslegeschrift 1 04Ç 939) or O, O-dialkylthiophosphoric acid esters of butenols (German Patent 1,058 044) to control insects. The effect of the compounds is satisfactory However not.

Es wurde gefunden, daß Verbindungen der Formel worin R und R' Methyl- oder Äthylgruppen und X ein Sauerstoff- oder Schwefelatom bedeuten, eine gute insektizide Wirkung haben.It has been found that compounds of the formula wherein R and R 'are methyl or ethyl groups and X is an oxygen or sulfur atom, have a good insecticidal effect.

Die Verbindungen können hergestellt werden durch Umsetzung der entsprechenden Phosphorestersäuren oder deren Salzen mit l-Äthylmercapto-2-chlor- oder -2-brom-buten-(3). Geeignete O,O-Dialkylesterphosphorsäuren sind beispielsweise die Dimethyl- oder Diäthylthiolphosphorsäure, ferner die Dimethyl- oder Diäthyldithiophosphorsäure. The compounds can be prepared by reacting the appropriate Phosphoric ester acids or their salts with 1-ethylmercapto-2-chloro- or -2-bromobutene (3). Suitable O, O-dialkyl ester phosphoric acids are, for example, the dimethyl or Diethylthiolphosphoric acid, and also dimethyl or diethyldithiophosphoric acid.

Von Salzen der O,O-Dialkylthiol- bzw. O,O-Dialkyldithiophosphorsäuren seien beispielsweise die Natrium-, Kalium-, Calcium-, Magnesium- und Ammoniumsalze der obengenannten Säuren erwähnt. Of salts of O, O-dialkylthiol or O, O-dialkyldithiophosphoric acids are for example the sodium, potassium, calcium, magnesium and ammonium salts of the acids mentioned above.

Die Umsetzung erfolgt durch Zusammengeben der beiden Reaktionskomponenten, wobei es gleichgültig ist, welche Komponente vorgelegt wird. The reaction takes place by combining the two reaction components, it does not matter which component is presented.

Als Wirkstoffe werden beispielsweise die folgenden Verbindungen genannt: Analysenwerte: Berechnet ... C 40,0, H 7,0, S32,0, P 10,3010; gefunden ... C 39,7, H 7,0, S 31,0, P 9,5°/o. Brechungsindex n2D = 1,554 Brechungsindex n200 = 1,502 Brechungsindex n2Do= 1,509 Die erfindungsgemäßen Mittel werden aus den Wirkstoffen durch Mischung mit üblichen Streckmitteln erhalten.The following compounds, for example, are mentioned as active ingredients: Analysis values: Calculated ... C 40.0, H 7.0, S32.0, P 10.3010; Found ... C 39.7, H 7.0, S 31.0, P 9.5%. Refractive index n2D = 1.554 Refractive index n200 = 1.502 Refractive index n2Do = 1.509 The agents according to the invention are obtained from the active ingredients by mixing them with customary extenders.

Das folgende Beispiel erläutert die Anwendung der erfindungsgemäßen Mittel. The following example explains the application of the invention Middle.

Beispiel Für die Versuche wurden die folgenden Stoffe verwendet: Vergleichssubstanz (deutsche Patentschrift 1 072 616) Vergleichssubstanz (deutsche Auslegeschrift 1046939) Wirkstoff I II III Dauerkontakt bei Taufliegen (Drosophila melano- gaster), 6 Stunden, LD50 in γ je 240 cm² ..... 2 500 200 Zuchtversuch mit Drosophila melanogaster, wirk- same Menge je 40 g Nährboden ............. 0,25 mg 4 mg 2 mg Wirkung gegen Spinnmilben (Tetranychus bima- culatus) auf Bohnen (Phaseolus multiflorus) mit wäßriger Emulsion ......................... 0,020/0 0,1 O/o - wirksam unwirksam Wirkung gegen Blattläuse (systemische Wirkung) 0,05°/0 - 0,1 O/o wirksam unwirksam Ein Vergleich des Wirkstoffs 1 mit den aus den Beispielen 5 und 7 der deutschen Patentschrift 1 058 044 bekannten Wirkstoffen ergab, daß die bekannten Wirkstoffe keine systemische Wirksamkeit haben.Example The following substances were used for the tests: Comparative substance (German patent specification 1 072 616) Comparative substance (German interpretation 1046939) Active ingredient I II III Permanent contact with fruit flies (Drosophila melano- gaster), 6 hours, LD50 in γ 240 cm² each ..... 2 500 200 Breeding trial with Drosophila melanogaster, effective same amount per 40 g nutrient medium ............. 0.25 mg 4 mg 2 mg Effect against spider mites (Tetranychus bima- culatus) on beans (Phaseolus multiflorus) with aqueous emulsion ......................... 0.020 / 0 0.1 O / o - effective ineffective Action against aphids (systemic action) 0.05% / 0 - 0.1% effective ineffective A comparison of active ingredient 1 with the active ingredients known from Examples 5 and 7 of German patent specification 1,058,044 showed that the known active ingredients have no systemic activity.

Claims (1)

Patentanspruch: Mittel zur Bekämpfung von Insekten, g e -kennzeichnet durch einen Gehalt an einer Verbindung der Formel worin R und R' Methyl- oder Äthylgruppen und X X ein Sauerstoff- oder Schwefelatom bedeuten.Claim: Agent for combating insects, characterized by a content of a compound of the formula wherein R and R 'are methyl or ethyl groups and XX is an oxygen or sulfur atom. In Betracht gezogene Druckschriften: Deutsche Auslegeschriften Nr. 1058044, 1046939, 1 072 616, 1 056 117, 1063148; Viliam T r e h y, Ref. Chem. Zbl., 1957, S.4944. Publications considered: German Auslegeschriften No. 1058044, 1046939, 1,072,616, 1,056,117, 1063148; Viliam T r e h y, Ref. Chem. Zbl., 1957, p.4944.
DEB59454A 1960-09-21 1960-09-21 Preparations for the control of insects Pending DE1173723B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB59454A DE1173723B (en) 1960-09-21 1960-09-21 Preparations for the control of insects

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB59454A DE1173723B (en) 1960-09-21 1960-09-21 Preparations for the control of insects

Publications (1)

Publication Number Publication Date
DE1173723B true DE1173723B (en) 1964-07-09

Family

ID=6972470

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB59454A Pending DE1173723B (en) 1960-09-21 1960-09-21 Preparations for the control of insects

Country Status (1)

Country Link
DE (1) DE1173723B (en)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1046939B (en) * 1956-04-21 1958-12-18 Bayer Ag Pest repellants
DE1056117B (en) * 1957-01-05 1959-04-30 Bayer Ag Process for the preparation of O, O-dialkylthiolphosphoric acid and -thiolthionophosphoric acid-S-gamma-cyanallyl esters
DE1058044B (en) * 1956-06-05 1959-05-27 Basf Ag Process for the preparation of O, O-dialkylphosphoric acid esters of substituted halobutenols, particularly suitable for pest control
DE1063148B (en) * 1957-09-24 1959-08-13 Bayer Ag Process for the preparation of O, O-dialkyl-S-propargyl-thio- or -dithiophosphoric acid esters
DE1072616B (en) * 1958-01-02 1960-01-07 Badische Anilin- &. Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhein Process for the preparation of 0,0-D'ialkylphosphoric acid esters of substituted butenols which are particularly suitable as pesticides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1046939B (en) * 1956-04-21 1958-12-18 Bayer Ag Pest repellants
DE1058044B (en) * 1956-06-05 1959-05-27 Basf Ag Process for the preparation of O, O-dialkylphosphoric acid esters of substituted halobutenols, particularly suitable for pest control
DE1056117B (en) * 1957-01-05 1959-04-30 Bayer Ag Process for the preparation of O, O-dialkylthiolphosphoric acid and -thiolthionophosphoric acid-S-gamma-cyanallyl esters
DE1063148B (en) * 1957-09-24 1959-08-13 Bayer Ag Process for the preparation of O, O-dialkyl-S-propargyl-thio- or -dithiophosphoric acid esters
DE1072616B (en) * 1958-01-02 1960-01-07 Badische Anilin- &. Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhein Process for the preparation of 0,0-D'ialkylphosphoric acid esters of substituted butenols which are particularly suitable as pesticides

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