US2585493A - Process for destroying pests comprising the application of the dibutyl acetal of aminoacetaldehyde to the pest - Google Patents

Process for destroying pests comprising the application of the dibutyl acetal of aminoacetaldehyde to the pest Download PDF

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Publication number
US2585493A
US2585493A US61140A US6114048A US2585493A US 2585493 A US2585493 A US 2585493A US 61140 A US61140 A US 61140A US 6114048 A US6114048 A US 6114048A US 2585493 A US2585493 A US 2585493A
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United States
Prior art keywords
aminoacetaldehyde
pest
application
dibutyl acetal
destroying pests
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Expired - Lifetime
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US61140A
Inventor
Emily M Owen
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GAF Chemicals Corp
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General Aniline and Film Corp
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Publication date
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Priority to US61140A priority Critical patent/US2585493A/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
    • 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
    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

Definitions

  • R-CHr-CH wherein R is hydrogen, NHz, C1, or C013 and R1 is an ethyl or'butyl group and R2 is a butyl, decyl or dodecyl group.
  • the compounds of the present invention have been found useful both for the destruction and inhibition of growth of soft-bodied insects, bacteria, fungi, worm pests such as nematodes and wireworms etc. and, for convenience, the material is herein designated as a biocide.
  • the following examples illustrate the use of certain of the compounds on bacteria, spores and aphids.
  • Example 1 Example 2 Using the procedure described in Example 1, it was found that a 100092 solution of the tetrabutyl acetal of iminodiacetaldehyde in /1o% acetone completely inhibited the germination of Sclerotinia fructz'cola spores.
  • Example 3 When a 0.1% solution of dibutyl acetal of aminoacetaldehyde in 10% acetone was tested by the agar cup plate method as described in U. S. D. A., Circular No. 193, an 8.0 mm. zone of inhibition was shown against Escherichia coli and a 1.5 mm. zone of inhibition against Staphylococcus aureus.
  • Example 4 A solution containing 0.5% by weight of the dibutyl acetal of 5, 8,fi-trichloropropionaldehyde in 50% acetone was sprayed on a potted nasturtium plant infested with Aphis rumicis. After 24 hours a mortality of of .the aphids was observed.
  • Example 5 A solution of 0.125% by weight of the dibutyl acetal of aminoacetaldehyde sprayed as in the above example gave 83% mortality of Aphis rumicls.
  • the acetals of the present invention are preferably used in solution in an organic solvent therefore which is also miscible in water such as ethyl alcohol and acetone.
  • the compounds may be employed with inert diluents and with carriers, in solution with various solvents, emulsifying agents, in water dispersions, etc. They may be applied as dusts, sprays, washes, aerosols, dipping solutions, etc.
  • a process for destroying pests which comprises applying thereto dibutyl acetal of aminoacetaldehyde.

Description

Patented Feb. 12, 1952 UNITED STATES PATENT OFFICE PROCESS FOR DESTROYING PESTS COM- PRISING THE APPLICATION OF THE DI- BUTYL HYDE TO THE PEST ACETAL OF AMINOACETALDE- Emily M. Owen, Easton, Pa., assignor to General Aniline & Film Corporation, New York, N. Y., a corporation of Delaware No Drawing. Application November 19, 1948, Serial No. 61,140
1 Claim.
R-CHr-CH wherein R is hydrogen, NHz, C1, or C013 and R1 is an ethyl or'butyl group and R2 is a butyl, decyl or dodecyl group.
Examples of some of these compounds include the following:
Table The compounds of the present invention have been found useful both for the destruction and inhibition of growth of soft-bodied insects, bacteria, fungi, worm pests such as nematodes and wireworms etc. and, for convenience, the material is herein designated as a biocide. The following examples illustrate the use of certain of the compounds on bacteria, spores and aphids.
Example 1 Example 2 Using the procedure described in Example 1, it was found that a 100092 solution of the tetrabutyl acetal of iminodiacetaldehyde in /1o% acetone completely inhibited the germination of Sclerotinia fructz'cola spores.
Example 3 When a 0.1% solution of dibutyl acetal of aminoacetaldehyde in 10% acetone was tested by the agar cup plate method as described in U. S. D. A., Circular No. 193, an 8.0 mm. zone of inhibition was shown against Escherichia coli and a 1.5 mm. zone of inhibition against Staphylococcus aureus.
Example 4 A solution containing 0.5% by weight of the dibutyl acetal of 5, 8,fi-trichloropropionaldehyde in 50% acetone was sprayed on a potted nasturtium plant infested with Aphis rumicis. After 24 hours a mortality of of .the aphids was observed.
Example 5 A solution of 0.125% by weight of the dibutyl acetal of aminoacetaldehyde sprayed as in the above example gave 83% mortality of Aphis rumicls.
The acetals of the present invention are preferably used in solution in an organic solvent therefore which is also miscible in water such as ethyl alcohol and acetone. However, the compounds may be employed with inert diluents and with carriers, in solution with various solvents, emulsifying agents, in water dispersions, etc. They may be applied as dusts, sprays, washes, aerosols, dipping solutions, etc.
I claim:
A process for destroying pests which comprises applying thereto dibutyl acetal of aminoacetaldehyde.
EMILY M. OWEN.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS OTHER REFERENCES Roarke et al.: U. S. D. A. Tech. Bull. No. 162, entitled Tests of Various Aliphatic Compounds as Fumigants, March 1929, p. 18.
US61140A 1948-11-19 1948-11-19 Process for destroying pests comprising the application of the dibutyl acetal of aminoacetaldehyde to the pest Expired - Lifetime US2585493A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3298906A (en) * 1964-11-02 1967-01-17 Du Pont Substituted acrolein acetals in plant protectant and nematocidal methods

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR711290A (en) * 1930-05-19 1931-09-07 Rhone Poulenc Sa Insecticide products
US2129025A (en) * 1935-12-07 1938-09-06 Winthrop Chem Co Inc Insecticide

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR711290A (en) * 1930-05-19 1931-09-07 Rhone Poulenc Sa Insecticide products
US2129025A (en) * 1935-12-07 1938-09-06 Winthrop Chem Co Inc Insecticide

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3298906A (en) * 1964-11-02 1967-01-17 Du Pont Substituted acrolein acetals in plant protectant and nematocidal methods

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