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GB814198A - New thiophosphoric acid esters and their use in the control of pests - Google Patents

New thiophosphoric acid esters and their use in the control of pests

Info

Publication number
GB814198A
GB814198A GB19734/55A GB1973455A GB814198A GB 814198 A GB814198 A GB 814198A GB 19734/55 A GB19734/55 A GB 19734/55A GB 1973455 A GB1973455 A GB 1973455A GB 814198 A GB814198 A GB 814198A
Authority
GB
United Kingdom
Prior art keywords
ethyl
sulphur
thiophosphate
benzyl
general formula
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
GB19734/55A
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 Schweiz AG
Original Assignee
Ciba 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 Ciba AG filed Critical Ciba AG
Publication of GB814198A publication Critical patent/GB814198A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
    • 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
    • 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
    • C07F9/16—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
    • 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
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/1653—Esters of thiophosphoric acids with arylalkanols
    • 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
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/177—Esters of thiophosphoric acids with cycloaliphatic alcohols
    • 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
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/201—Esters of thiophosphorus acids
    • 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
    • C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2408—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyalkyl 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)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (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)

Abstract

The invention comprises compounds of the general formula <FORM:0814198/IV (b)/1> in which one Z represents sulphur and the remaining Z's represent oxygen, R represents an alkyl radical containing not more than 4 carbon atoms and R1 represents a cycloaliphatic e.g. cyclohexyl, or araliphatic radical e.g. benzyl, or a radical of a heterocyclic compound free from enolisable ketone or thio ketone groups, e.g. tetrahydrofurfuryl, R2 represents an aliphatic radical which may be substituted with halogen thiocyanogen cyano, nitro ether or ester group and "alkeylene" represents an alkylene radical containing not more than 4 carbon atoms. They may be prepared by reacting a compound of the general formula <FORM:0814198/IV (b)/2> with a compound of the general formula Hal-alkylene-S-R2, or a compound of the general formula <FORM:0814198/IV (b)/3> with one of the general formula R1-Hal. R, R1, R2 and "alkylene" having the meanings given above and Me representing a metal atom, or by the additive combination of sulphur with a derivative of phosphorous acid of the general formula <FORM:0814198/IV (b)/4> Examples are given of the preparation of (1) tetra - hydro - furfuryl - ethyl - (ethylthioethyl) thiophosphate by treating the potassium salt of tetrahydrofurfurylethyl - thiophosphoric acid <FORM:0814198/IV (b)/5> with b - chloro - diethyl sulfide; (2) benzyl-ethyl - (ethylthio - ethyl) thiophosphate from benzyl-ethyl-potassium thiophosphate and b -chloro - ethyl - ethyl sulphide or by transesterifying diethyl phosphite with b -hydroxydiethyl-sulphide and converting with sulphur and K2CO3 and treating the product with benzyl chloride; (3) cyclohexyl-ethyl-(ethyl thio ethyl) thiophosphate from b -chloro diethyl sulphide and cyclohexyl ethyl-potassium thiophosphate; (4) the addition product of sulphur and benzyl ethyl-(b -ethyl-thioethyl) phosphite; (5) the addition product of sulphur and parachlorobenzyl-ethyl-(ethyl-thioethyl) phosphite.ALSO:Pesticidal preparations comprise as active ingredients thiophosphoric acid esters of the general formula <FORM:0814198/VI/1> in which one Z represents sulphur and the remaining Z's represent oxygen, R represents an alkyl radical containing not more than 4 C atoms, R1 represents a cycloaliphatic, e.g. cyclohexyl, araliphatic, e.g. benzyl, or heterocyclic radical free from enolizable ketone or thioketane groups, e.g. tetrahydrofurfural, R2 represents an aliphatic radical which may be substituted with halogen, thiocyanogen, cyano nitro ether or ester groups, and "alkylene" represents an alkylene radical containing not more than 4 C atoms and a solid or liquid diluent or solvent. Other insecticides and/or fungicides may be incorporated in the composition. Specified compounds are tetrahydrofurfurylethyl - (ethyl - thioethyl) - thiophosphate, benzyl - ethyl - (ethylthio - ethyl) - thiophosphate, cyclohexyl - ethyl - (ethyl - thioethyl) - thiophosphate, the addition product of sulphur and para - chlorobenzyl - ethyl - (ethyl - thioethyl) - thio phosphite, and the addition product of sulphur and benzyl ethyl-(b -ethyl-thioethyl)-phosphite.
GB19734/55A 1954-09-29 1955-07-07 New thiophosphoric acid esters and their use in the control of pests Expired GB814198A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH814198X 1954-09-29

Publications (1)

Publication Number Publication Date
GB814198A true GB814198A (en) 1959-06-03

Family

ID=4538793

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19734/55A Expired GB814198A (en) 1954-09-29 1955-07-07 New thiophosphoric acid esters and their use in the control of pests

Country Status (4)

Country Link
BE (2) BE539661A (en)
DE (1) DE1012112B (en)
FR (2) FR1164210A (en)
GB (1) GB814198A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1114490B (en) 1958-09-20 1961-10-05 Bayer Ag Process for the preparation of phosphonic acid-O-ethyl-thiolesters
NL288076A (en) * 1962-01-24

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2571989A (en) * 1949-09-28 1951-10-16 Bayer Ag Neutral esters of thiophosphoric acid

Also Published As

Publication number Publication date
DE1012112B (en) 1957-07-11
FR1164210A (en) 1958-10-07
BE539661A (en)
FR1164211A (en) 1958-10-07
BE539662A (en)

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