US2416004A - Insect control - Google Patents

Insect control Download PDF

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Publication number
US2416004A
US2416004A US440880A US44088042A US2416004A US 2416004 A US2416004 A US 2416004A US 440880 A US440880 A US 440880A US 44088042 A US44088042 A US 44088042A US 2416004 A US2416004 A US 2416004A
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Prior art keywords
nitriles
carbon atoms
unsaturated
area
nitrile
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US440880A
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Walter E Hall
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Shell Development Co
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Shell Development Co
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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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles

Definitions

  • pyrethrum and rotenone are both derived from plants grown primarily in foreign countries and are therefore expensive and not always obtainable in the desired quantities.
  • unsaturated alkyl nitriles having 14 to 30 carbon atoms are edective as insecticides
  • Unsaturated nitriles having i8 to 20 carbon atoms are more edective as insecticides than those with 14 or 30.
  • the unsaturated alkyl radicals may be straight, branched or allcarbocyclic, such as cetenylic, oleic, eicosenoic, lauryl cyclohexenylic, cetyl cyclohexenylic, cetenyl cyclohexylic, cetenyl cyclohexenylic, hexenyl dicyclohexylic, etc., radicals.
  • the alkyl radical may contain additional toxic radicals. such as chlorine, sulfide, amino, lecto, hydroxyl, nitro, cyanate, etc., radicals.,
  • additional toxic radicals such as chlorine, sulfide, amino, lecto, hydroxyl, nitro, cyanate, etc., radicals.
  • nitriles are the straight-chain aliphatic nitrlles having a single olenic double bond, e. s., cetenylic, oleic, erucic, etc., ntriles.
  • the method of testing used in evaluating the instant compounds as inothproof agents is tmovvn as the ,whole circle testI and is fully described in Industrial and Engineering Chemistry, Analytical Edition, vol. 2, No. d, page 365, under the title "Methods oi testing mothproo com pounds.
  • the method consists of placing a twoinch square of woolen. material, treated with the mothproong agent being tested,- in a petri dish with ten black carpet beetle larvae (Attagenus which substances are repellentthe fabric. in the set ci tests shown in the table,
  • the vvoolen squares were observed four weeks after addition ol the larvae to the dishes.
  • the woolen squares were treated by spraying either one-half or one cubic centimeter of the insecti cide onto the squares lfrom a distance of it inches, immediately hanging the squares up to dry, and aging them by hanging in a screened case in the insecticide laboratory until used for testing.
  • the cacy oi the treatment is determined by the observed damage to the vlooien square and the amount of frase and lint produced, the latterl being a quantitative measure of the feeding done by the larvae.
  • the repellent action ot the nitriles is indicated by the results in the following table which show that the larvae of the Black Carpet Beetle were deterred from feeding rather than eating and becoming poisoned. Testing was done in the same manner as described before and the sample tested consisted oi 5% oleic nitriles, 95% numeral spirits. Results were as follows:
  • the unsaturated nitriles oi the instant invention are useful in conjunction with well-known insecticides and iungicides.
  • the nitriles may be used in combination with py- ⁇ rethrum, rotenone, lead arsenate, nicotine, thiocyanates, isothiocyanates, copper naphthenate, or the like.
  • the unsaturated nitriles may be applied to plants and animals in a variety of ways.
  • the nitriles may be dissolved in a light hydrocarbon oil such as kerosene or kerosene distillate with or without the addition of other insecticides and sprayed.
  • a light hydrocarbon oil such as kerosene or kerosene distillate
  • other insecticides such as kerosene or kerosene distillate.
  • from about 1% to 25% of the unsaturated nitriles are used in suchspray oils.
  • the nitriles may be dissolved in plant spray oils and emulsiiied in water to produce sprayable emulsions.
  • the common emulsiiying agents such as glycerol mono-oleate, amine salts, sulfated and sulfonated fatty and numeral oils, soaps, and the like, may be used in combination with such sprays.
  • the nitriles themselves without the ad dition of oil, may be emuisified and used in plant spray insecticides.
  • the nitriles may also be adsorbed by finely divided solid materials, such as wood iiour, talc, clay, sulfur or carbon black, and used as dusting insecticides.
  • An insect control composition comprising a predominant amount of mineral spirits and containing from 1% to 25% of an unsaturated aliphatic ntrile having from 16 to 20 carbon atoms.
  • a method of mothproofing wool comprising applying to it a small amount of a composition containing as the active ingredient an unsaturated aliphatic nitrile having from 16 to 20 carbon atoms.
  • a method of mothproong wool comprising applying to it a small amount of a composition comprising a major proportion of mineral spirits and containing from 1% to 25% of oleic nitrile.
  • a method of repeiling insects from an area comprising treating the area with a composition 'containing oieonitrile as an active essentia1 ingredient.
  • a method of combating insects from an area comprising treating the area with a composition containing as an active insecticidal ingredient an unsaturated aliphatic nitrile having from 16 to 20 carbon atoms.
  • a method of combating insects from an area 4 ,f comprising treating the areat'vith a composition containing as an active insecticidal ingredient an unsaturated straight chain aliphatic nitrile having from 16 to 20 carbon atoms.
  • a method of combating insects from an area comprising treating thearea with a composition containing as an active insecticidal ingredient an unsaturated branched-chain aliphatic nitrile having from 16 to 20 carbon atoms.
  • a method of combating insects from an area comprising treating the area with a composition containing as an active insecticidal ingredient an unsaturated alicarbocyclic nitrile having from 16 to 20 carbon atoms.
  • a method of combating insects from an area comprising treating the area with a composition containing as an active insecticidal ingredient a mono-olenic aliphatic nitrile having from 16 to 20 carbon atoms.
  • a method of combating insects from an area comprising treating the area with a composition containing as an active insecticida] ingredient a mono-oleiinic straight-chain aliphatic nitrile having from 16 to 20 carbon atoms.
  • An insect control composition comprising a predominant amount of mineral spirits and a minor amount of an unsaturated aliphatic nitrile having from 16 to 20 carbon atoms.
  • An insect control composition comprising a predominantl amount of mineral spirits and a minor amount of oieic nitriie, sufiicient in amount to render said composition toxic to insect life.
  • An insect control composition comprising a vehicle and dispersed therein a minor amount of oleic nitrile, suiiicient in amount to render said composition toxic to insect life.

Description

l I or tomo, or both.
ceases eelt., i iv sans msec
wat a. aan, ver, accionar sneu l veloot Compa Sian i" e f @limi @f Mmm wir actuation as se, iste. al No. ddt@ This invention 'deals with a new insect control composition oi' great utility and is ,f-:u concerned with substances suitable for use in household sprays.
Among the best known and moet useful insecticides'at present are pyrethrum and rotenone. These are both derived from plants grown primarily in foreign countries and are therefore expensive and not always obtainable in the desired quantities.
It is an object of the prt invention to provide an insecticide which can be manufactured from readily available and inexpensive domestic materials. It is a further object of this invention to provide an insecticide which, although not iastacting, is repellent and toxic. A special object is to provide an insecticide oi unusual effectiveness in the control of the larvae of moths. Other and further objects will appear as the description proceeds.
It has now been found that unsaturated alkyl nitriles having 14 to 30 carbon atoms are edective as insecticides, Unsaturated nitriles having i8 to 20 carbon atoms are more edective as insecticides than those with 14 or 30. The unsaturated alkyl radicals may be straight, branched or allcarbocyclic, such as cetenylic, oleic, eicosenoic, lauryl cyclohexenylic, cetyl cyclohexenylic, cetenyl cyclohexylic, cetenyl cyclohexenylic, hexenyl dicyclohexylic, etc., radicals. If desired, the alkyl radical may contain additional toxic radicals. such as chlorine, sulfide, amino, lecto, hydroxyl, nitro, cyanate, etc., radicals., Thus ricinoleic nitrile is among the compounds of this invention.
i A single nitrile or mixtures oi' several may be used for the purpose of the invention. Preferred nitriles are the straight-chain aliphatic nitrlles having a single olenic double bond, e. s., cetenylic, oleic, erucic, etc., ntriles.
Although i't will be understood that the nitriles of the instant invention have wide application in the control oi various insects, the examples set out in the table to follow are confined to the control of clothes moths.
The method of testing used in evaluating the instant compounds as inothproof agents is tmovvn as the ,whole circle testI and is fully described in Industrial and Engineering Chemistry, Analytical Edition, vol. 2, No. d, page 365, under the title "Methods oi testing mothproo com pounds. The method consists of placing a twoinch square of woolen. material, treated with the mothproong agent being tested,- in a petri dish with ten black carpet beetle larvae (Attagenus which substances are repellentthe fabric. in the set ci tests shown in the table,
the vvoolen squares were observed four weeks after addition ol the larvae to the dishes. The woolen squares were treated by spraying either one-half or one cubic centimeter of the insecti cide onto the squares lfrom a distance of it inches, immediately hanging the squares up to dry, and aging them by hanging in a screened case in the insecticide laboratory until used for testing. The cacy oi the treatment is determined by the observed damage to the vlooien square and the amount of frase and lint produced, the latterl being a quantitative measure of the feeding done by the larvae.
The results shown in the table following show a comparison between oleic nitrile and four moth proofing insecticides of commerce:
Observed Semois Mothproong Amount fg'ig damage to number agent sprayed produced wool test piece M zo sughi.
l 9 Moderate $5 20 uch.
l 16 Do. l/ 19 Do. 1 23 Do. it 2c Do, l 25 D0. 4 Slight.
3D 95% (small). io o l 4 None. ll Mineral spirits.. 1 s? Verymuch.
The repellent action ot the nitriles is indicated by the results in the following table which show that the larvae of the Black Carpet Beetle were deterred from feeding rather than eating and becoming poisoned. Testing was done in the same manner as described before and the sample tested consisted oi 5% oleic nitriles, 95% numeral spirits. Results were as follows:
cant or repellent, the unsaturated nitriles oi the instant invention are useful in conjunction with well-known insecticides and iungicides. Thus the nitriles may be used in combination with py-` rethrum, rotenone, lead arsenate, nicotine, thiocyanates, isothiocyanates, copper naphthenate, or the like.
The unsaturated nitriles may be applied to plants and animals in a variety of ways. For use as household insecticides, the nitriles may be dissolved in a light hydrocarbon oil such as kerosene or kerosene distillate with or without the addition of other insecticides and sprayed. Ordinarily, from about 1% to 25% of the unsaturated nitriles are used in suchspray oils.
. For use on plants, the nitriles may be dissolved in plant spray oils and emulsiiied in water to produce sprayable emulsions. The common emulsiiying agents such as glycerol mono-oleate, amine salts, sulfated and sulfonated fatty and numeral oils, soaps, and the like, may be used in combination with such sprays. In the same manner, the nitriles themselves, without the ad dition of oil, may be emuisified and used in plant spray insecticides. The nitriles may also be adsorbed by finely divided solid materials, such as wood iiour, talc, clay, sulfur or carbon black, and used as dusting insecticides.
I claim as my invention:
1 An insect control composition comprising a predominant amount of mineral spirits and containing from 1% to 25% of an unsaturated aliphatic ntrile having from 16 to 20 carbon atoms.
2. A method of mothproofing wool comprising applying to it a small amount of a composition containing as the active ingredient an unsaturated aliphatic nitrile having from 16 to 20 carbon atoms.
3. A method of mothproong wool comprising applying to it a small amount of a composition comprising a major proportion of mineral spirits and containing from 1% to 25% of oleic nitrile.
4. A method of repeiling insects from an area. comprising treating the area with a composition 'containing oieonitrile as an active essentia1 ingredient.
5. A method of combating insects from an area comprising treating the area with a composition containing as an active insecticidal ingredient an unsaturated aliphatic nitrile having from 16 to 20 carbon atoms.
6. A method of combating insects from an area 4 ,f comprising treating the areat'vith a composition containing as an active insecticidal ingredient an unsaturated straight chain aliphatic nitrile having from 16 to 20 carbon atoms.
'l'. A method of combating insects from an area comprising treating thearea with a composition containing as an active insecticidal ingredient an unsaturated branched-chain aliphatic nitrile having from 16 to 20 carbon atoms.
8. A method of combating insects from an area comprising treating the area with a composition containing as an active insecticidal ingredient an unsaturated alicarbocyclic nitrile having from 16 to 20 carbon atoms.
9. A method of combating insects from an area comprising treating the area with a composition containing as an active insecticidal ingredient a mono-olenic aliphatic nitrile having from 16 to 20 carbon atoms.
10. A method of combating insects from an area comprising treating the area with a composition containing as an active insecticida] ingredient a mono-oleiinic straight-chain aliphatic nitrile having from 16 to 20 carbon atoms.
l1. An insect control composition comprising a predominant amount of mineral spirits and a minor amount of an unsaturated aliphatic nitrile having from 16 to 20 carbon atoms.
12.An insect control composition comprising a predominantl amount of mineral spirits and a minor amount of oieic nitriie, sufiicient in amount to render said composition toxic to insect life.
13. An insect control composition comprising a vehicle and dispersed therein a minor amount of oleic nitrile, suiiicient in amount to render said composition toxic to insect life.
WALTER E. HALL.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date Re.20,689 Bousquet oct. 4, 193s 1,991,955 Ralston Feb. 19, 1935 2,037,389 Nicodemus Apr. 14, 1956 2,205,076 Wortz June 18, 1940 2,206,351 Greenhalgh July 2, 1940 2,280,850 Ralston et al Apr. 28, 1942
US440880A 1942-04-26 1942-04-26 Insect control Expired - Lifetime US2416004A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2620290A (en) * 1947-10-23 1952-12-02 Du Pont Alpha, omega-thiocyanoalkanol insecticidal compositions and their use
US3012932A (en) * 1959-02-19 1961-12-12 Standard Oil Co Compositions and methods employing insecticidal oil soluble organic carbylamines

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1991955A (en) * 1934-04-13 1935-02-19 Armour & Co Process of pyrolytically treating higher fatty acid substances
US2037389A (en) * 1932-02-03 1936-04-14 Ig Farbenindustrie Ag Nitriles of higher unsaturated fatty acids and a process of preparing them
USRE20689E (en) * 1938-04-05 Structural assembly
US2205076A (en) * 1937-11-06 1940-06-18 Du Pont Preparation of long-chain aliphatic mononitriles
US2206351A (en) * 1936-12-29 1940-07-02 Ici Ltd Preparation of aliphatic acid nitriles
US2280850A (en) * 1939-09-05 1942-04-28 Armour & Co Insect repellent containing nitriles

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE20689E (en) * 1938-04-05 Structural assembly
US2037389A (en) * 1932-02-03 1936-04-14 Ig Farbenindustrie Ag Nitriles of higher unsaturated fatty acids and a process of preparing them
US1991955A (en) * 1934-04-13 1935-02-19 Armour & Co Process of pyrolytically treating higher fatty acid substances
US2206351A (en) * 1936-12-29 1940-07-02 Ici Ltd Preparation of aliphatic acid nitriles
US2205076A (en) * 1937-11-06 1940-06-18 Du Pont Preparation of long-chain aliphatic mononitriles
US2280850A (en) * 1939-09-05 1942-04-28 Armour & Co Insect repellent containing nitriles

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2620290A (en) * 1947-10-23 1952-12-02 Du Pont Alpha, omega-thiocyanoalkanol insecticidal compositions and their use
US3012932A (en) * 1959-02-19 1961-12-12 Standard Oil Co Compositions and methods employing insecticidal oil soluble organic carbylamines

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