DE1034410B - Insecticidal agent - Google Patents

Insecticidal agent

Info

Publication number
DE1034410B
DE1034410B DEC13026A DEC0013026A DE1034410B DE 1034410 B DE1034410 B DE 1034410B DE C13026 A DEC13026 A DE C13026A DE C0013026 A DEC0013026 A DE C0013026A DE 1034410 B DE1034410 B DE 1034410B
Authority
DE
Germany
Prior art keywords
diethyl
hours
phosphonate
trichloroacetyl
destruction
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
DEC13026A
Other languages
German (de)
Inventor
Martin J Diamond
Gustave K Kohn
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.)
California Spray Chemical Corp
Original Assignee
California Spray Chemical Corp
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 California Spray Chemical Corp filed Critical California Spray Chemical Corp
Publication of DE1034410B publication Critical patent/DE1034410B/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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/28—Titanium compounds
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4062—Esters of acids containing the structure -C(=X)-P(=X)(XR)2 or NC-P(=X)(XR)2, (X = O, S, Se)
    • C07F9/4065—Esters of acids containing the structure -C(=X)-P(=X)(XR)2, (X = O, S, Se)
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

DEUTSCHESGERMAN

Die Erfindung betrifft die Verwendung der durch tropfenweise Zugabe von Triäthylphosphit zu Trichloracetylchlorid im Molverhältnis 1 :1 erhaltenen Reaktionsprodukte als Insektizides Mittel.The invention relates to the use of trichloroacetyl chloride by adding triethyl phosphite dropwise reaction products obtained in a molar ratio of 1: 1 as an insecticidal agent.

Es ist bekannt, daß man durch Umsetzung von Triäthylphosphit mit Trichloracetylchlorid Diäthyltrichloracetylphosphonat der folgenden Formel erhältIt is known that diethyl trichloroacetylphosphonate can be obtained by reacting triethyl phosphite with trichloroacetyl chloride of the following formula

O OO O

C2H5Ox χ πC 2 H 5 O x χ π

2 5 \ T il ίο 2 5 \ T il ίο

/P-C-CCl3
C2H5O'/ PC-CCl 3
C 2 H 5 O '

wobei das Triäthylphosphit dem Trichloracetylchlorid zugegeben werden muß, da bei umgekehrter Reihenfolge der Zugabe ein anderer Reaktionsverlauf eintritt. Es ist jedoch nicht bekannt, daß das bei dieser Umsetzung erhältliche Reaktionsgemisch bzw. das aus diesem Gemisch isolierbare Diäthyltrichloracetylphosphonat ein hervorragendes Insektizid darstellt, das die insektizide und insbesondere die miticide Wirksamkeit der nächsten Homologen des Diäthyltrichloracetylphosphonats sowie der als Schädlingsbekämpfungsmittel bekannten Halogenacetyldiphosphonate weit übertrifft.the triethyl phosphite must be added to the trichloroacetyl chloride, since the reverse order The course of the reaction changes after the addition. However, it is not known that that obtainable from this reaction The reaction mixture or the diethyl trichloroacetylphosphonate which can be isolated from this mixture is an excellent one Insecticide represents the insecticidal and especially the miticidal effectiveness of the next Homologues of diethyl trichloroacetylphosphonate and the halogen acetyldiphosphonates known as pesticides far exceeds.

Das erfindungsgemäß als Insektizid zu verwendende Diäthyltrichloracetylphosphonat kann dadurch hergestellt werden, daß man 54 g Trichloracetylchlorid in einen 200 ecm fassenden Dreihalskolben, der mit einem Thermometer, einem Rührer, Tropftrichter und einem Auslaß für die entwickelten Gase versehen ist, gibt und tropfenweise 50 g Triäthylphosphit zusetzt.The diethyl trichloroacetylphosphonate to be used as an insecticide according to the invention can thereby be produced be that 54 g of trichloroacetyl chloride in a 200 ecm three-necked flask, which is with a thermometer, a stirrer, dropping funnel and an outlet for the evolved gases, and drop by drop 50 g of triethyl phosphite are added.

Dabei wird mit einem Eiswasserbad auf eine Anfangstemperatur von 1O0C gekühlt. Die Temperatur steigt auf einen Höchstwert von 350C. Die Reaktion ist stark exotherm und wird durch Kühlung mit dem Eisbad gesteuert. Here is cooled with an ice water bath to an initial temperature of 1O 0 C. The temperature rises to a maximum of 35 ° C. The reaction is strongly exothermic and is controlled by cooling with an ice bath.

Nachdem das gesamte Phosphit zugesetzt ist, wird die Lösung 1 bis lx/2 Stunden erhitzt, bis. die Temperatur 1050C erreicht hat. Es werden 84,5 g einer klaren farblosen Flüssigkeit erhalten. Bei der Destillation im Vakuum geht die Hauptfraktion bei 2,7 mm Hg zwischenAfter all of the phosphite has been added, the solution is heated for 1 to 1 x / 2 hours until. the temperature has reached 105 ° C. 84.5 g of a clear, colorless liquid are obtained. When distilling in vacuo, the main fraction goes between at 2.7 mm Hg

C2H5Ox IlC 2 H 5 O x II

C2H5O-^P + Cl-C-CCl3 C2H6O C 2 H 5 O- ^ P + Cl-C-CCl 3 C 2 H 6 O

Die hervorragenden Insektiziden Eigenschaften des Diäthyltrichloracetylphosphonats zeigen die nachfolgend aufgeführten Vergleichs versuche, die mit Diäthyltrichloracetylphosphonat, Diäthyldichloracetylphosphonat, Diäthylmonochloracetylphosphonat und Diäthylacetylphosphonat durchgeführt wurden. Die Herstellung dieser Insektizides MittelThe excellent insecticidal properties of diethyl trichloroacetylphosphonate are shown below Listed comparison experiments with diethyl trichloroacetylphosphonate, diethyldichloroacetylphosphonate, diethylmonochloroacetylphosphonate and diethyl acetylphosphonate were performed. The manufacture of these insecticidal agents

Anmelder:Applicant:

California Spray-Chemical Corporation, Richmond, Calif. (V. St. A.)California Spray-Chemical Corporation, Richmond, Calif. (V. St. A.)

Vertreter: Dr. W. Beil, Rechtsanwalt, Frankfurt/M.-Höchst, Antoniterstr. 36Representative: Dr. W. Beil, lawyer, Frankfurt / M.-Höchst, Antoniterstr. 36

Beanspruchte Priorität: V. St. v. Amerika vom 20. Mai 1955Claimed priority: V. St. v. America May 20, 1955

Martin J. Diamond und Gustave K. Kohn,Martin J. Diamond and Gustave K. Kohn,

Berkeley, Calif. (V. St. Α.), sind als Erfinder genannt wordenBerkeley, Calif. (V. St. Α.), Have been named as inventors

108 und 114,6° C in Form eines klaren farblosen Destillats über. Die weitere Reinigung durch nochmaliges Destillieren ergibt ein Produkt mit einem Siedepunkt von 106,5 bis 1080C bei einem Druck von 1,9 mm Hg. Das Produkt, das Diäthyltrichloracetylphosphonat, besaß einen Brechungsindex von w14'5 = 1,4648. Die Analyse ergab die folgenden Werte:108 and 114.6 ° C in the form of a clear colorless distillate. Further purification by repeated distillation results in a product having a boiling point 106.5 to 108 0 C at a pressure of 1.9 mm Hg. The product, which Diäthyltrichloracetylphosphonat, had a refractive index of w 14 '5 = 1.4648. The analysis resulted in the following values:

Berechnet GefundenCalculated Found

C 25,39% 25,62%C 25.39% 25.62%

H 3,52% 3,66%H 3.52% 3.66%

Cl 37,57% 37,60%Cl 37.57% 37.60%

O 22,58%O 22.58%

P 10,94% 10,7 o/,P 10.94% 10.7 o /,

C2H5O 31,74% 31,92%C 2 H 5 O 31.74% 31.92%

Molekulargewicht 283,5 275Molecular weight 283.5 275

Die Reaktion erfolgte nach der folgenden Gleichung:The reaction took place according to the following equation:

C2H5OC 2 H 5 O

C2H5OC 2 H 5 O

O OO O

j Ijj Ij

^P-C-CCl, + C2H5Cl^ PC-CCl, + C 2 H 5 Cl

Homologen kann durch Umsetzung von Triäthylphosphit mit den geeignet substituierten Acetylchloriden erfolgen.Homologs can be made by reacting triethyl phosphite with the appropriately substituted acetyl chlorides.

Die Versuche wurden an doppelt gefleckten MilbenThe experiments were carried out on double-spotted mites

Tetranychus bimaculatus Harvey unter Anwendung einer modifizierten Blatt-Scheiben-Versuchsmethode, die vonTetranychus bimaculatus Harvey using a modified leaf and disc test method developed by

E. H. Siegler in Journal Economic Entomology, Bd. 40,E. H. Siegler in Journal Economic Entomology, Vol. 40,

809 577/414809 577/414

Claims (1)

S. 280 (1947), beschrieben ist, ausgeführt. Bei diesen Versuchen wurden 2 bis' 4 cm2 große Teile natürlich befallener primärer Blätter von Ford-Hook-Lima-Bohnen-P. 280 (1947). In these experiments 2 to 4 cm 2 parts of naturally infected primary leaves of Ford-Hook-Lima-bean- Konzentration in °/oConcentration in ° / o Diäthylacetylphosphonat Diethylacetylphosphonate Diäthylmonochloracetylphosphonat ..Diethyl monochloroacetylphosphonate .. Diäthyldichloracetylphosphonat Diethyl dichloroacetyl phosphonate Diäthyltrichloracetylphosphonat Diethyl trichloroacetyl phosphonate Prozentuale Vernichtung bei ausgewachsenen MilbenPercentage destruction in adult mites 0,10.1 0,030.03 0,010.01 0,0030.003 6868 ' —'- —- —- 100100 9494 1414th —- 100100 9494 2222nd —- 100100 100100 100100 100100
pflanzen mit SO bis 100 Milben je Blatteil mit Aceton-Wasser-Lösungen der Testverbindung von verschiedenen Konzentrationen in Berührung gebracht. Die behandelten Blattsegmente wurden dann getrocknet und 24 Stunden auf feuchte Papiertücher in Petrischalen gebracht. Nach 24 Stunden wurde die prozentuale Vernichtung durch Auszählen bestimmt. Nach diesem Verfahren wurden die nebenstehenden Ergebnisse erhalten.plant with SO to 100 mites per leaf part with acetone-water solutions brought into contact with the test compound at various concentrations. The treated Leaf segments were then dried and placed on moist paper towels in petri dishes for 24 hours. After 24 hours, the percent destruction was determined by counting. According to this procedure the results below were obtained. Lo PATENTANSPKUGH: Lo PATENTANSPKUGH: Verwendung der durch tropfenweise Zugabe von Triäthylphosphit zu Trichloracetylchlorid im Molverhältnis 1:1 erhaltenen Reaktionsprodukte als Insektizides Mittel.Use of the by dropwise addition of triethyl phosphite to trichloroacetyl chloride in a molar ratio 1: 1 obtained reaction products as an insecticidal agent. In Betracht gezogene Druckschriften:
Schweizerische Patentschrift Nr. 303 952;
USA.-Patentschrift Nr. 2 491 920.Considered publications:
Swiss Patent No. 303 952;
U.S. Patent No. 2,491,920.
DEC13026A 1955-05-20 1956-05-16 Insecticidal agent Pending DE1034410B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US814010XA 1955-05-20 1955-05-20

Publications (1)

Publication Number Publication Date
DE1034410B true DE1034410B (en) 1958-07-17

Family

ID=22163910

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC13026A Pending DE1034410B (en) 1955-05-20 1956-05-16 Insecticidal agent

Country Status (4)

Country Link
DE (1) DE1034410B (en)
FR (1) FR1149408A (en)
GB (1) GB814010A (en)
NL (2) NL95664C (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3500610A (en) * 1962-03-07 1970-03-17 Eastman Kodak Co Apparatus for coating an article with a liquid substantially free from discrete immiscible matter
US4339443A (en) * 1978-09-22 1982-07-13 Fbc Limited Compounds and compositions

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2491920A (en) * 1946-05-16 1949-12-20 Du Pont Diesters of 1-ketophosphonic acids
CH303952A (en) * 1951-09-25 1954-12-31 Ciba Geigy Process for the manufacture of a pesticide.

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2491920A (en) * 1946-05-16 1949-12-20 Du Pont Diesters of 1-ketophosphonic acids
CH303952A (en) * 1951-09-25 1954-12-31 Ciba Geigy Process for the manufacture of a pesticide.

Also Published As

Publication number Publication date
FR1149408A (en) 1957-12-26
GB814010A (en) 1959-05-27
NL95664C (en)
NL207293A (en)

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