GB817360A - Chloromethylated o:o-dialkyl-thiophosphoric acid esters and a process for their manufacture - Google Patents

Chloromethylated o:o-dialkyl-thiophosphoric acid esters and a process for their manufacture

Info

Publication number
GB817360A
GB817360A GB3001757A GB3001757A GB817360A GB 817360 A GB817360 A GB 817360A GB 3001757 A GB3001757 A GB 3001757A GB 3001757 A GB3001757 A GB 3001757A GB 817360 A GB817360 A GB 817360A
Authority
GB
United Kingdom
Prior art keywords
product
production
reaction
thionothiol
distillation
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.)
Expired
Application number
GB3001757A
Inventor
Otto Scherer
Helmut Hahn
Gerhard Staehler
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst 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 Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB817360A publication Critical patent/GB817360A/en
Expired 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
    • C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl

Abstract

The invention comprises chloromethylated O,O-dialkyl thiophosphoric acid esters of the general formula (RO)(R1O)P(S)XCH2Cl in which R and R1 each stand for CH3 or C2H5 and X is oxygen or sulphur. They may be obtained by reacting the alkali metal or ammonium salts of the appropriate O,O-dialkyl thiophosphoric acids with chloro - bromomethane. The reaction is suitably carried out with an excess of chlorobromo-methane and an inert solvent may be present, e.g. methanol, ethanol, acetone or tetrahydrofurane. The reaction is generally carried out below 100 DEG C. and preferably at 50-70 DEG C. A small amount of an alkali metal iodide may be added to the reaction mixture to increase the yield of the product. When the reaction is complete the bromide formed is filtered off and excess chlorobromo-methane is recovered by distillation and this may be used again for further batches. The product is obtained by distillation of the residue. Examples are given for the production of: (1) O,O - diethyl - thionothiol - phosphoric acid S-chloromethyl ester; (2) O,O-dimethyl-thionothiol - phosphoric acid - S - chloromethyl ester and (3) O,O - diethyl - thiono - phosphoric acid-O-chloromethyl ester. In the examples for the production of products (1) and (2) the potassium salt of the O,O-dialkyl thiophosphoric acid is used and in the case of product (3) the ammonium salt is used. The products are stated to be effective as insecticides and to be valuable as intermediates for the production of other insecticides. Some bis - (O,O - diethyl - thionothiol-phosphoryl)-formal is also formed in one example for the production of product (1) and remains as residue after distillation of the product.
GB3001757A 1955-12-31 1957-09-24 Chloromethylated o:o-dialkyl-thiophosphoric acid esters and a process for their manufacture Expired GB817360A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF19209A DE1015794B (en) 1955-12-31 1955-12-31 Process for the preparation of chloromethylated O, O-dialkylthiophosphoric acid esters

Publications (1)

Publication Number Publication Date
GB817360A true GB817360A (en) 1959-07-29

Family

ID=7089242

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3001757A Expired GB817360A (en) 1955-12-31 1957-09-24 Chloromethylated o:o-dialkyl-thiophosphoric acid esters and a process for their manufacture

Country Status (5)

Country Link
CH (1) CH351953A (en)
DE (1) DE1015794B (en)
FR (1) FR1163684A (en)
GB (1) GB817360A (en)
NL (2) NL220830A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2410958A1 (en) * 1977-12-09 1979-07-06 Vyzk Ustav Agrochem INSECTICIDES, ACARICIDES AND OVICIDES BASED ON O, O-DIALCOYL-S-CHLOROMETHYL DITHIOPHOSPHATES
US4191757A (en) 1969-07-16 1980-03-04 The Murphy Chemical Company Limited 5-Chloromethyl diethylphosphorothiolothionate as a soil insecticide

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1949629A (en) * 1928-04-17 1934-03-06 American Cyanamid Co Di-thiophosphate compounds
US2266514A (en) * 1938-09-09 1941-12-16 American Cyanamid Co Esters of dithiophosphoric acids

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4191757A (en) 1969-07-16 1980-03-04 The Murphy Chemical Company Limited 5-Chloromethyl diethylphosphorothiolothionate as a soil insecticide
FR2410958A1 (en) * 1977-12-09 1979-07-06 Vyzk Ustav Agrochem INSECTICIDES, ACARICIDES AND OVICIDES BASED ON O, O-DIALCOYL-S-CHLOROMETHYL DITHIOPHOSPHATES

Also Published As

Publication number Publication date
FR1163684A (en) 1958-09-30
NL220830A (en)
NL96707C (en)
DE1015794B (en) 1957-09-19
CH351953A (en) 1961-02-15

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