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US2418652A - Insecticidal compositions - Google Patents

Insecticidal compositions Download PDF

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Publication number
US2418652A
US2418652A US445106A US44510642A US2418652A US 2418652 A US2418652 A US 2418652A US 445106 A US445106 A US 445106A US 44510642 A US44510642 A US 44510642A US 2418652 A US2418652 A US 2418652A
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US
United States
Prior art keywords
oil
insecticidal
active
water
depositing
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
US445106A
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English (en)
Inventor
Kenneth E Maxwell
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.)
Shell Development Co
Original Assignee
Shell Development Co
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Filing date
Publication date
Application filed by Shell Development Co filed Critical Shell Development Co
Priority to US445106A priority Critical patent/US2418652A/en
Application granted granted Critical
Publication of US2418652A publication Critical patent/US2418652A/en
Priority to FR949710D priority patent/FR949710A/fr
Priority to NL133271A priority patent/NL67374C/xx
Priority to DEN2085A priority patent/DE835960C/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents

Definitions

  • a primary object of this invention is to provide an additive for insecticidal compositions capable of yielding increased deposits of said materials when sprayed on foliage, fruits, or dormant trees.
  • mineral oils which have long been used as insecticidal sprays, are usually applied in the form of an emulsion with water.
  • foliage spraying they are ordinarily emulsified with 96-99% of water, and in dormant spraying with as little as 95% of water.
  • the water acts as a carrying agent for the oil and effects a distribution of the oil over the plant.
  • the water also carries considerable quantities of the oil from the sprayed object.
  • a further object is to provide a depositing agent which will cause the insecticide to adhere firmly to the fruit or foliage.
  • insecticidal material refers to mineral oils either with or without the addition of toxicants.
  • toxicants may comprise pyrethrum, rotenone, derris resins, nicotine, aliphatic thiocyanates, dinitro cresols, dinitro phenols, ketones, ketols, halogenated hydrocarbons such as chlorinated naphthalenes, cresylic acid, alkyl amines, pine Oils, etc.
  • Emulsified oil globules as Well as wet leaf surfaces, normally possess negative electrostatic charges.
  • the mineral oils are normally emulsified for spray purposes either by mechanical agitation in the spray machine 2 alone or by such agitation and addition of oilsoluble emulsifiers.
  • Such emulsifiers may comprise alkyl sulfonates and sulfates such as petroleum sulfonic acids and their oil-soluble sodium, potassium, or ammonium salts; fatty and naphthenic acid soaps; certain fatty acid esters of polyhydric alcohols, polymerized animal and vegetable oils and nonionic emulsifiers such as monostearyl, lauryl, and oleyl ethers of polyethylene glycol. Most of these commonly used agents are anion-active and some few are electrically neutral. They therefore either further increase the negative potential on oil globules and leaf surfaces or else have no, or but slight, effect on the electrostatic charge.
  • the magnitude of the negative charge is directly related to the stability of the emulsion on the leaf and, consequently, emulsions containing conventional emulsifiers do not readily break to deposit the insecticidal material.
  • the quantity of cation-active additives must be kept below a certain maximum in Order to be effective for increasing deposits of the insecticidal material.
  • the additives are inefiective as depositing agents.
  • the critical feature of the quantity added is believed to be due to such a complete reversal of the charge on the oil globules when more than certain amounts are added that an emulsion results of positively charged oil globules of sufficient stability to be carried off by the water despite the attraction ofiered by the opposite charge of the leaves.
  • emulsifying amount of cationic additive should be employed, i. e. an amount of the additive less than that which will render an emulsion of the mineral oil. insecticidal material more stable than prior to the addition of my additive.
  • effective quantities of my additive may range from about .01% to 1% by weight of the oil, depending upon the particular additive chosen.
  • a preferred amount for several cationic surface-active compounds has been found to be about .1%.
  • the additive should be soluble to the desired extent in either the oil than %,preferably 1% or less;
  • a preferred group of cation surface-active contains a lipophilic group sucl ⁇ as, and preferably, a hydrocarbon group of at least eight carbon atoms.
  • the or ganic radical may also contain a chain comprisformation.
  • the anion may be the anion of any acid having hydrophilic properties being devoid of surface activity and being stable and inert under normal conditions of use, or it may be a hydroxyl group.
  • the requirement of surface activity excludes such acids as oil-soluble sulfonic acids and the requirement of inertness excludes chromic, perboric, chloric, etc.
  • the quaternary ammonium and phosphonium compounds may be represented by the general formula:
  • X stands for nitrogen, or phosphorus
  • R is a hydrocarbon or substituted hydrocarbon cal may be replaced by a chloride, iodide, acetate, sulfate, nitrate, etc., substituent. bus, for example, cetyl trimethyl ammonium chloride (C16H33 (CH3)3NC1) 2.
  • C16H33 (CH3)3NC1) cetyl trimethyl ammonium chloride
  • Pyridinium salts may be prepared by reacting alkyl halides such as cetyl bromide with pyridine:
  • Triethyl hexadecyl phosphonium bromide (C2H5)3-P(BI)C16H33, dodecyl-trimethyl-p h S- phonium bromide, C12H25(CI-Iz)sPBr, or similar compounds.
  • R represents hydrogen, alkyl, aryl, or substituted alkyl or aryl radicals
  • Z is a hydrophilic acid anion or hydroxyl ion.
  • ternary sulphonium salts which are similar except for the lesser valence of the nuclear atom to the quaternary ammonium and phosphonium salts described under the above general formula.
  • Me.Et.S.(SO4ME) clans or other tetravalent sulfur compounds such as di-ethyl octadecyl sulphonium chloride may be mentioned as illustrative of suitable sulphonium salts.
  • a preferred group of cation surface-active depositing agents may be prepared from the basic condensation products of organic carboxylic acids and amino-alcohols or diamines, or similar com-' pounds having a lipophilic group of at least eight carbon atoms and being cation surface-active Wetting agents.
  • This type of basic compound forms salts by reaction with hydrophilic acids, for example monobasic acids, such as hydrochloric and hydrobromic acid, acetic acid, propionic acid, etc., dibasic acids, such as malonic, malic, maleic glutaric, etc., or, under proper conditions, with alkyl or aryl substituted mineral acids, which salts are cation-active.
  • hydrophilic acids for example monobasic acids, such as hydrochloric and hydrobromic acid, acetic acid, propionic acid, etc., dibasic acids, such as malonic, malic, maleic glutaric, etc., or, under proper conditions, with alkyl or aryl substituted mineral acids, which salts are cation-active.
  • hydrophilic acids for example monobasic acids, such as hydrochloric and hydrobromic acid, acetic acid, propionic acid, etc., dibasic acids, such as malonic, malic, maleic glutaric, etc., or, under proper conditions,
  • R is a hydrocarbon or acyl group containing a terminal hydrocarbon group of at least eight and preferably ten carbon atoms, depending on the number and strength of the hydrophiiic groups in the molecule, and which may contain non-functional substituents; and R1 and R2 are hydrogen or hydrocarbon radicals such as hydrogen, alkyl, aryl, aralkyl, etc., radicals, which may contain hydroxy or alkoxy radicals, halide atoms, etc.
  • Compounds of the type R- 3-1 I-cHr0Hr-N ogm)i 2.
  • Compounds of the type R-( J-o-cmcHr-NR'1 Especially suitable compounds for my purpose are the salts of hydrophilic acids, e. g., malic acid, and the basic condensation products of high molecular weight carboxylic acids or mixtures of different high molecular weight carboxylic acids,
  • the salt of malic acid and the acid amides produced by condensing a mixture of paimitic and stearic acid with ethanol ethylene diamine is particularly efiective for my purpose.
  • This salt will for convenience, be referred to hereinafter as the malate of EXAMPLE I
  • the efiectiveness of the depositing agents was determined under conditions simulating field practice. Spray oils to be tested both with and without the herein described depositing agents were emulsified with water in a small field-type spray machine capable of operating at spraying pressures up to 1000 lbs.
  • EXAMPLE II 20 ursed ivHarnd.asC-NH-CH2CHzNHCHzCHzOH (i. e. the salt of malic acid and the acid amides produced by condensing a mixture of palmit-ic and stearic acids with alkanol ethylene diamine) a cation surface-active compound, were emulsifled in the laboratory spray apparatus as described above. For each test, 250 ml, of emulsion were removed from thespray tank, placed in a modifiedCassia flask, and the oil allowed to separate. for an hour. After standing for this period,
  • Emulsifyzng conditions Oil dosage, per cent concentration 1.67 Pressure, lbs/sq. in 500 Circulation time, sec 30 11 Oil contained 2% cresylic acid by volume as a mutual solvent for the depositing agent.
  • insecticidal compositions of my invention may contain other additives, such as antipenetrants like glyceryl oleate, glyceryl mono-oleate, aluminum naphthenate, visco resins, aluminum stearate, triethanolamine, cottonseed oil and similar fatty oils, etc., spreading agents such as blood albumin and/or with other known depositing agents like ketones, etc.
  • antipenetrants like glyceryl oleate, glyceryl mono-oleate, aluminum naphthenate, visco resins, aluminum stearate, triethanolamine, cottonseed oil and similar fatty oils, etc.
  • spreading agents such as blood albumin and/or with other known depositing agents like ketones, etc.
  • An insecticidal composition essentially comprising a mineral. oil, and. insecticidal toxicant, and between about 0.01% and about 1.0% (by weight of the oil) of a cation surface-active depositing agent, said composition being capable of forming an unstable emulsion with water.
  • An insecticidal composition essentially comprising a mineral oil, and insecticidal toxicant, and a cation surface-active depositing agent in an amount of the order of about 0.1% by weight Results Grams 8f the malate of lgerccntt Oil.
  • the attached drawing shows the amount of deposit obtained with the spray oil containing various amounts of the malate of under conditions as described in Example I above.
  • An insecticidal composition essentially comprising a mineral oil, and insecticidal toxicant, and between about 0.01% and about 1.0% (by weight of the oil) of the malate of the condensation product of ethanol ethylene diamine and a mixture of stearic and palmitic acids, said composition being capable of forming an unstable emulsion with water.
  • An insecticidal composition essentially comprising a mineral oil, and insecticidal toxicant, and between about 0.01% and about 1.0% (by weight of the oil) of a cation surface-active depositing agent and a minor amount, based on the ,Weight of said oil, of a mutual solvent for said cation surface-active depositing agent, said composition being capable of forming an unstable emulsion with water.
  • An unstable insecticidal emulsion of a mineral oil in water essentially comprising said mineral oil, an insecticidal toxicant, water, and between about 0.0l% and about 1.0% (by weight of the oil) of a cation surface-active depositing agent.

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US445106A 1942-05-28 1942-05-28 Insecticidal compositions Expired - Lifetime US2418652A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US445106A US2418652A (en) 1942-05-28 1942-05-28 Insecticidal compositions
FR949710D FR949710A (fr) 1942-05-28 1947-07-08 Compositions insecticides
NL133271A NL67374C (de) 1942-05-28 1947-07-14
DEN2085A DE835960C (de) 1942-05-28 1950-09-29 Schaedlingsbekaempfungsmittel

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US445106A US2418652A (en) 1942-05-28 1942-05-28 Insecticidal compositions

Publications (1)

Publication Number Publication Date
US2418652A true US2418652A (en) 1947-04-08

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Application Number Title Priority Date Filing Date
US445106A Expired - Lifetime US2418652A (en) 1942-05-28 1942-05-28 Insecticidal compositions

Country Status (4)

Country Link
US (1) US2418652A (de)
DE (1) DE835960C (de)
FR (1) FR949710A (de)
NL (1) NL67374C (de)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2500122A (en) * 1947-12-20 1950-03-07 American Cyanamid Co Emulsions
US2554192A (en) * 1947-11-01 1951-05-22 Socony Vacuum Oil Co Inc Herbicidal composition
US2940896A (en) * 1956-02-23 1960-06-14 Pennsalt Chemicals Corp Quaternary ammonium and phosphoramide ester attractants and insect control therewith
EP0039144A2 (de) * 1980-04-18 1981-11-04 Imperial Chemical Industries Plc Zum elektrodynamischen Vernebeln geeignete pestizide Formulierungen und zu deren Herstellung geeignete Lösung
US5773016A (en) * 1995-01-27 1998-06-30 S C. Johnson & Son, Inc. Insecticidally-active water-in oil-out emulsions and insecticidally active compositions derived therefrom

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1405856A (en) * 1919-09-13 1922-02-07 Bob White Chemical Corp Insecticide
GB393276A (en) * 1931-11-25 1933-05-25 Ici Ltd Manufacture of emulsions, dispersions, and the like
US1934057A (en) * 1928-10-31 1933-11-07 Standard Oil Dev Co Insecticide
US1940646A (en) * 1927-10-19 1933-12-19 Standard Oil Dev Co Insecticide and process of making the same
US2134917A (en) * 1935-07-11 1938-11-01 Benjamin R Harris Antiparasitic compositions
US2139277A (en) * 1938-02-23 1938-12-06 Du Pont Dialkyl cyclohexylamine salts of higher alkyl sulphates
US2151788A (en) * 1937-10-15 1939-03-28 Alframine Corp Acid addition compounds of higher fatty acid amides
US2202387A (en) * 1938-03-26 1940-05-28 Givaudan Delawanna Inc Mineral oil solutions
US2206928A (en) * 1928-02-17 1940-07-09 Ig Farbenindustrie Ag Production of condensation products
US2362760A (en) * 1943-01-12 1944-11-14 Shell Dev Insecticidal compositions

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1405856A (en) * 1919-09-13 1922-02-07 Bob White Chemical Corp Insecticide
US1940646A (en) * 1927-10-19 1933-12-19 Standard Oil Dev Co Insecticide and process of making the same
US2206928A (en) * 1928-02-17 1940-07-09 Ig Farbenindustrie Ag Production of condensation products
US1934057A (en) * 1928-10-31 1933-11-07 Standard Oil Dev Co Insecticide
GB393276A (en) * 1931-11-25 1933-05-25 Ici Ltd Manufacture of emulsions, dispersions, and the like
US2134917A (en) * 1935-07-11 1938-11-01 Benjamin R Harris Antiparasitic compositions
US2151788A (en) * 1937-10-15 1939-03-28 Alframine Corp Acid addition compounds of higher fatty acid amides
US2139277A (en) * 1938-02-23 1938-12-06 Du Pont Dialkyl cyclohexylamine salts of higher alkyl sulphates
US2202387A (en) * 1938-03-26 1940-05-28 Givaudan Delawanna Inc Mineral oil solutions
US2362760A (en) * 1943-01-12 1944-11-14 Shell Dev Insecticidal compositions

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2554192A (en) * 1947-11-01 1951-05-22 Socony Vacuum Oil Co Inc Herbicidal composition
US2500122A (en) * 1947-12-20 1950-03-07 American Cyanamid Co Emulsions
US2940896A (en) * 1956-02-23 1960-06-14 Pennsalt Chemicals Corp Quaternary ammonium and phosphoramide ester attractants and insect control therewith
EP0039144A2 (de) * 1980-04-18 1981-11-04 Imperial Chemical Industries Plc Zum elektrodynamischen Vernebeln geeignete pestizide Formulierungen und zu deren Herstellung geeignete Lösung
EP0039144A3 (de) * 1980-04-18 1982-05-05 Imperial Chemical Industries Plc Zum elektrodynamischen Vernebeln geeignete pestizide Formulierungen und zu deren Herstellung geeignete Lösung
US5773016A (en) * 1995-01-27 1998-06-30 S C. Johnson & Son, Inc. Insecticidally-active water-in oil-out emulsions and insecticidally active compositions derived therefrom

Also Published As

Publication number Publication date
NL67374C (de) 1950-09-15
FR949710A (fr) 1949-09-07
DE835960C (de) 1952-04-07

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