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
  • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic 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 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
• • 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
  • C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
  • C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
• • 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
  • C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
  • C07F9/655363—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a six-membered ring
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S424/00—Drug, bio-affecting and body treating compositions
  • Y10S424/08—Systemic pesticides

Definitions

• the new compounds of this invention may be represented by the following formula:
• R and R are lower alkyl radicals
• R is selected from the group consisting of hydrogen and alkyl radicals having from 1 to 5 carbon atoms
• R? is selected from the group consisting of methylene and carbonyl
• n is an integer from 1 to 2
• the groups represented by X are independently selected from the group consisting of oxygen and sulfur, and X and X are independently selected from the group consisting of oxygen and sulfur, at least one of them being sulfur
• Y is selected from the group consisting of alkylene radicals having from 1 to 3 carbon atoms and phenylene
• Z is selected from the group consisting of hydrogen and carbethoxy.
• Suitable alkyl radicals for R and R include methyl, ethyl, propyl, isopropyl, :amyl, octyl, and the like.v
• Preparation of the compounds of the present invention is accomplished by reacting a phosphorylated aldehyde or ketone with a glycol or monoor dimercaptan, preferably in the presence of an acid catalyst. This reaction may be represented by the following equation:
• R, R R X, X X Y, Z, and n are as described hereinbefore.
• a solvent such as benzene and ethyl ether may be used but is not strictly essential to the process.
• suitable acid catalysts for the reaction are boron trifiuoride etherate and gaseous HCl.
• the reaction may be carried out at temperatures between 0 C. and 100 C. but preferably between about 20 C.
• Pesticidal activity for the compounds of the foregoing examples is illustrated in Table I wherein the percentage kill is reported for a specified quantity of the candidate pesticide expressed in micrograms (hereafter termed the bio-assay test), or for a percentage concentration in aque- XA 10 E MPLES CH ous dispersion (hereafter termed the screening test).
• a H a slanted line is used to separate the percentage kill, shown a )2 2 -C s on the left, and the percentage concentraion or quantity,
• Table I Compound House flies, American Milkweed Confused Two-spotted Two-spotted Two-spotted (example number) percent; roach, bug, percent flour beetle, mite post mite eggs, mite systemic,
• the following new compounds may also be prepared in reasonable yields when using the desired phosphorylated aldehyde or ketone with the corresponding glycol or mercaptan.
• This solution was diluted with water containing 0.015% Vatsol (a sulfonate-type wetting agent) and 0.005% Methocel (methyl cellulose) as emulsifiers, the amount of water being sufficient to dilute the active ingredients to a concentration of 0.1% or below.
• Vatsol a sulfonate-type wetting agent
• Methocel methyl cellulose
• the bean plants were infested with several hundred mites and then sprayed to run-off with an aqueous test dispersion prepared as described above. Sprayed plants were transferred to a greenhouse and held for 14 days.
• the miticidal and ovicidal activity of the test compounds were determined after 7 to 14 days. The 14 day reading was necessary for evaluating ovicidal action. Percentage mortality is reported, as shown in Table I, for both post embryonic and embryonic forms.
• pinto bean plants were placed in bottles containing 200 ml.
• the compounds may also be used in the form of emulsions, non-aqueous emulsions, wettable powders, vapors, and dusts, as may be best suited for the conditions of use.
• the toxic material may even be used in a pure undiluted form.
• pest is used herein in the restricted sense generally recognized in the art as applying to the lower forms of life customarily controlled .by chemical means and excluding the higher animals, the vertebrates, for example, rodents, birds, and larger forms which are more commonly controlled by mechanical means such as traps. In its broadest usage, the term refers to both the destructive and annoying household and plant organisms, especially .the parasites and pathogens. It will be apparent to one skilled in the art that the activity demonstrated on the selected insects and mites is indicative of activity in various species and orders not specifically shown.
• R and R are lower alkyl, R is selected from the group consisting of hydrogen and alkyl having from 1 to 5 carbon atoms, R is selected from the group consisting of methylene and carbonyl, n is an integer from 1 to 2; the groups represented by X are independently selected from the group consisting of oxygen and sulfur, and X and X are independently selected from the group consisting of oxygen and sulfur, at least one of them being sulfur; Y is selected from the group consisting of alkylene having from 1 to 3 carbon atoms and phenylene; and Z is selected from the group consisting of hydrogen and carbethoxy.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Health & Medical Sciences (AREA)
• Biochemistry (AREA)
• Molecular Biology (AREA)
• Dentistry (AREA)
• Engineering & Computer Science (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Plant Pathology (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

Priority Applications (8)

Applications Claiming Priority (1)

Publications (1)

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Family Applications (1)

Country Status (6)

Cited By (7)

Citations (8)

• 0
  • BE BE633592D patent/BE633592A/xx unknown
  • NL NL294012D patent/NL294012A/xx unknown
• 1962
  • 1962-06-15 US US202686A patent/US3247223A/en not_active Expired - Lifetime
• 1963
  • 1963-05-30 GB GB21743/63A patent/GB1025569A/en not_active Expired
  • 1963-06-13 CH CH738263A patent/CH428764A/de unknown
  • 1963-06-13 CH CH1710966A patent/CH430320A/de unknown
  • 1963-06-14 BR BR149862/63A patent/BR6349862D0/pt unknown

Patent Citations (8)

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