US3316145A - O, o-dimethyl s-(1-succinimidoethyl) phos-phorodithioate and insecticidal compositions containing the same - Google Patents

O, o-dimethyl s-(1-succinimidoethyl) phos-phorodithioate and insecticidal compositions containing the same Download PDF

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Publication number
US3316145A
US3316145A US424843A US42484365A US3316145A US 3316145 A US3316145 A US 3316145A US 424843 A US424843 A US 424843A US 42484365 A US42484365 A US 42484365A US 3316145 A US3316145 A US 3316145A
Authority
US
United States
Prior art keywords
dimethyl
succinimidoethyl
concentrate
toxicant
phosphorodithioate
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 - Lifetime
Application number
US424843A
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English (en)
Inventor
Albert H Haubein
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.)
BOOTS HERCULES AGROCHEMICALS Co A PARTNERSHIP OF
Original Assignee
Hercules LLC
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 Hercules LLC filed Critical Hercules LLC
Priority to US424843A priority Critical patent/US3316145A/en
Priority to IL24877A priority patent/IL24877A/en
Priority to GB556/66A priority patent/GB1098548A/en
Priority to FR46803A priority patent/FR1469250A/fr
Priority to BE674914D priority patent/BE674914A/xx
Priority to NL6600295A priority patent/NL6600295A/xx
Priority to ES0321588A priority patent/ES321588A1/es
Priority to CH26768A priority patent/CH500229A/fr
Priority to DE19661695128 priority patent/DE1695128A1/de
Priority to CH31166A priority patent/CH453790A/fr
Priority to DK13966AA priority patent/DK124411B/da
Application granted granted Critical
Publication of US3316145A publication Critical patent/US3316145A/en
Assigned to BOOTS HERCULES AGROCHEMICALS CO., A PARTNERSHIP OF DE reassignment BOOTS HERCULES AGROCHEMICALS CO., A PARTNERSHIP OF DE ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: HERCULES INCORPORATED
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/5537—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom the heteroring containing the structure -C(=O)-N-C(=O)- (both carbon atoms belong to the heteroring)
    • 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

Definitions

  • 0,0-dimethyl S'(1-succinimidoethyl) phosphorodithioate is a biodegradable insecticide having a long residual toxicity.
  • Example 1 To 38 parts of N-vinyl succinimide in 40 parts of benzene was added 53.7 parts dimethyl dithiophosphoric acid in about parts of benzene dropwise over a 0.5 hour period. The resulting solution was heated at 80 C. under reflux for 6 hours, cooled and washed at 35 C. with water and 5% aqueous sodium bicarbonate solution. On cooling below room temperature, 39.3 parts crystalline product separated. After distilling off the benzene and adding a little ether, an additional crop of 30.5 parts crystalline product was obtained.
  • the reaction between the N-vinyl succinimide and 0,0-dimethyl dithiophosphoric acid takes place at a temperature within the range of 25-l20 C.
  • the reaction between N-a-chloroethyl succinimide and 0,0-dimethyl dithiophosphoric acid, or a salt thereof such as the ammonium salt, also yields the product of this invention.
  • Solvents for the latter reaction include acetone and acetonitrile in addition to benzene or toluene.
  • the 0,0-dimethyl S-( l-succinimidoethyl) phosphorodithioate of this invention is useful as a toxicant in insecticide compositions for many types of insects and is used preferably as a dust or as an aqueous emulsion.
  • Dusts are formulated from a dust concentrate or from It is common practice for a formulator to dilute a dust concentrate with a clay or similar powdered solid to the desired dilution for application.
  • the dust concentrate when compounded with a wetting Ialgent, is a wettable powder, which is emulsifiable in the eld.
  • Aqueous emulsions are formulated by a formulator from a liquid concentrate.
  • the formulator will use either a liquid concentrate containing the toxicant and a surface-active dispersing agent, or a liquid concentrate, water, and a surface-active agent.
  • a liquid concentrate containing a surface-active agent will be used by the man in the field who wishes to prepare aqueous emulsions economically.
  • the concentrate is preferably a composition of the toxicant of this invention and a non-volatile adjuvant which is solid, as in the case of dusts, or is liquid, as in the case here an aqueous emulsion is produced or in the case here a formulator mixes the liquid concentrate with dust v form a more dilute dust.
  • a concentrate of toxicant 1d a volatile adjuvant such as a volatile organic solvent ill be useful also for combination with a surface-active djuvant by a formulator of concentrates.
  • the concentration of the toxicant in a concentrate will e 10-90% in the case where a volatile organic solvent used, and 25-90% where there is no volatile organic olvent.
  • the solid adjuvant of the composition is selected accordinging to the properties desired from such solids as :lays, fullers earth, diatomaceous earth, rosin, petroleum iydrocarbon insoluble pine wood resins, and surfaceictive dispersing agents.
  • the solid adjuvant will thus in nany cases have surface-active, spreading or sticking properties and, in some cases, will be used with water or organic solvent to aid in the mixing process.
  • the liquid adjuvant of the composition is selected from the non-volatile liquids such as petroleum oils, paraffin, oils, lubricating oils and rosin oils, and volatile liquids such as toluene, benzene, Xylenes, volatile petroleum fractions, acetone, methyl ethyl ketone, and diacetone alcohol.
  • non-volatile liquids such as petroleum oils, paraffin, oils, lubricating oils and rosin oils
  • volatile liquids such as toluene, benzene, Xylenes, volatile petroleum fractions, acetone, methyl ethyl ketone, and diacetone alcohol.
  • the concentrate containing a surface-active agent will contain usually 0.01 to 2 times as much surface-active agent as toxicant and other components to be dispersed in formation of an aqueous emulsion, and preferably 0.05 to 0.5 times as much surface-active agent as material to be dispersed.
  • the concentrate which is a solution of all components such as a concentrate of toxicant and surfaceactive agent which is soluble in organic solvents preferably also contains a volatile organic solvent in an amount in the range of 0.1 to 10 times the weight of toxicant when necessary to improve fluidity.
  • the concentrate of toxicant and liquid non-volatile adjuvant generally contains 5-25% surface-active agent to aid in emulsification.
  • a concentrate containing a surface-active agent is, by well known technique, formed into water-in-oil or oil-in-water emulsions. For the former, -25% surface-active agent is used and, for the latter, -20% is used.
  • a concentrate containing toxicant, non-volatile adjuvant, and surface-active agent is emulsified in the field without further diluting but it is, at times, advantageous to dilute this concentrate with oil containing a surface-active agent when it is desired to obtain dilute water-in-oil, i.e., invert, emulsions.
  • the surface-active agents which are used are any of those anionic, cationic or non-ionic surface-active agents well known in the art. See Chemistry of Insecticides, Fungicides and Herbicides (Donald E. H. Frear, 2nd ed. 194-8, pages 280-7).
  • the surface-active agents which are particularly suitable are the polyoxyethylene compounds such as reaction products of alcohols or amines with ethylene oxide. Other surface-active agents and methods of using them for various types of emulsions are to be found in Surface Active Agents-Their Chem istry and Technology, Anthony M. Schwartz and James W. Perry, Interscience Publishers Inc., New York, 1949,
  • a concentrate of equal parts each of acetone, 0,0- dimethyl S-(l-succinimidoethyl) phosphorodithioate and Tween 20 was prepared and added to distilled water, with rapid stirring, to form emulsions of various concentrations from 0.05% to 0.0005% toxicant.
  • a 0.025% emulsion gave kill of housefiies.
  • An 0.0025% emulsion gave a 100% kill of Mexican bean beetle.
  • a 0.005% emulsion gave a 100% kill of pea aphids.
  • a 0.0005 emulsion gave a 100% kill of two-spotted mites.
  • the residual activity shows the superiority of the toxicant of this invention when applied to the habitats of mosquitoes.
  • the toxicant of this invention while high in residual activity on the habitats of many insects, is nevertheless not in the persistent class since it is biodegradable, for example, in soil.
  • the 0,0-dimethyl S-(l-succinimidoethyl) phosphorodithioate of this invention can be used in combination with other insecticides where desired.
  • the other insecticide need not be biodegradable since the biodegradability of the present insecticide will act as an improver of the properties of the combination.
  • An insecticide concentrate comprising 0,0-dimethyl S-(l-succinimidoethyl) phosphorodithioate as a toxicant and a non-volatile dispersing adjuvant therefor.
  • An insecticide concentrate comprising 0,0-dimethy1 S-(l-succinimidoethyl) phosphorodithioate as -a toxicant and a solid non-volatile dispersing adjuvant therefor.
  • An insecticide concentrate comprising 0,0-dimethyl S-(l-succinimidoethyl) phosphorodithioate as a toxicant and a surface-active dispersing agent in an amount effective for dispersing the toxicant in water.
  • An insecticide concentrate comprising 0,0-dimethyl S-(l-succinimidoethyl) phosphorodithioate as a toXicant, an organic solvent for the toxicant and a surface-active dispersing agent soluble in said solvent in an amount effective for dispersing the toxicant in water.
  • An aqueous emulsion comprising a major amount of water and a minor but insecticidally effective amount of 0,0-dimethyl S-(l-succinimidoethyl) phosphorodithioate and a surface-active dispersing agent.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US424843A 1965-01-11 1965-01-11 O, o-dimethyl s-(1-succinimidoethyl) phos-phorodithioate and insecticidal compositions containing the same Expired - Lifetime US3316145A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
US424843A US3316145A (en) 1965-01-11 1965-01-11 O, o-dimethyl s-(1-succinimidoethyl) phos-phorodithioate and insecticidal compositions containing the same
IL24877A IL24877A (en) 1965-01-11 1965-12-27 O,o-dimethyl s-(alpha-succinimidoethyl)phosphorodithioate and insecticidal compositions containing the same
GB556/66A GB1098548A (en) 1965-01-11 1966-01-05 An organic phosphorodithioate compound
FR46803A FR1469250A (fr) 1965-01-11 1966-01-07 omicron, omicron-diméthyl s-(1-succinimidoéthyl) phosphorodithioate et composition insecticide le contenant
NL6600295A NL6600295A (da) 1965-01-11 1966-01-10
ES0321588A ES321588A1 (es) 1965-01-11 1966-01-10 Un procedimiento para preparar una composicion insecticida.
BE674914D BE674914A (da) 1965-01-11 1966-01-10
CH26768A CH500229A (fr) 1965-01-11 1966-01-11 Procédé de préparation du O,O-diméthyl-S-(1-succinimidoéthyl)-phosphorodithioate
DE19661695128 DE1695128A1 (de) 1965-01-11 1966-01-11 Schaedlingsbekaempfungsmittel
CH31166A CH453790A (fr) 1965-01-11 1966-01-11 Composition insecticide
DK13966AA DK124411B (da) 1965-01-11 1966-01-11 Fosfordithioat til anvendelse i insekticider.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US424843A US3316145A (en) 1965-01-11 1965-01-11 O, o-dimethyl s-(1-succinimidoethyl) phos-phorodithioate and insecticidal compositions containing the same

Publications (1)

Publication Number Publication Date
US3316145A true US3316145A (en) 1967-04-25

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US424843A Expired - Lifetime US3316145A (en) 1965-01-11 1965-01-11 O, o-dimethyl s-(1-succinimidoethyl) phos-phorodithioate and insecticidal compositions containing the same

Country Status (10)

Country Link
US (1) US3316145A (da)
BE (1) BE674914A (da)
CH (1) CH453790A (da)
DE (1) DE1695128A1 (da)
DK (1) DK124411B (da)
ES (1) ES321588A1 (da)
FR (1) FR1469250A (da)
GB (1) GB1098548A (da)
IL (1) IL24877A (da)
NL (1) NL6600295A (da)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE930446C (de) * 1953-02-09 1955-07-18 Bayer Ag Verfahren zur Herstellung von Thiophosphorsaeureestern
US2902493A (en) * 1955-05-13 1959-09-01 Bayer Ag Thiophosphoric acid esters and process for their production
GB869399A (en) * 1958-07-15 1961-05-31 Basf Ag O.o-dialkyl-thiol-and o.o-dialkyl-dithio-phosphoric acid esters of lactams and thiolactams

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE930446C (de) * 1953-02-09 1955-07-18 Bayer Ag Verfahren zur Herstellung von Thiophosphorsaeureestern
US2902493A (en) * 1955-05-13 1959-09-01 Bayer Ag Thiophosphoric acid esters and process for their production
GB869399A (en) * 1958-07-15 1961-05-31 Basf Ag O.o-dialkyl-thiol-and o.o-dialkyl-dithio-phosphoric acid esters of lactams and thiolactams

Also Published As

Publication number Publication date
BE674914A (da) 1966-07-11
DK124411B (da) 1972-10-16
IL24877A (en) 1969-11-12
CH453790A (fr) 1968-03-31
GB1098548A (en) 1968-01-10
NL6600295A (da) 1966-07-12
DE1695128A1 (de) 1970-12-10
FR1469250A (fr) 1967-02-10
ES321588A1 (es) 1967-01-01

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