CA1133390A - Higher alcohol toxicants - Google Patents
Higher alcohol toxicantsInfo
- Publication number
- CA1133390A CA1133390A CA304,411A CA304411A CA1133390A CA 1133390 A CA1133390 A CA 1133390A CA 304411 A CA304411 A CA 304411A CA 1133390 A CA1133390 A CA 1133390A
- Authority
- CA
- Canada
- Prior art keywords
- alcohol
- carrier
- octanol
- pentanol
- hexadecyl
- 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
Links
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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
-
- 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
- A01N31/02—Acyclic compounds
-
- 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
- A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic 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
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
HIGHER ALCOHOL TOXICANTS
ABSTRACT OF THE DISCOSURE
Higher alcohols the logarithm of whose partition coeffi-cient between n-octanol and water is at least 0.61 have been found to exhibit pediculicidal and/or ovicidal activity.
ABSTRACT OF THE DISCOSURE
Higher alcohols the logarithm of whose partition coeffi-cient between n-octanol and water is at least 0.61 have been found to exhibit pediculicidal and/or ovicidal activity.
Description
M- 8559 (for. flg. ) .
i~333~V
BAC~G~OUND. 0~: THE INVENTION
~ . . . . .
There are only a relatively few pediculicides whlch are commercially a~ailable *oday. The most popular pediculicidal -toxicants ar~ Lindane (gamma ~enzene hexachloride)~ alathion . .
- [~S-1,2-dicarbethoxyethyl)-O,O-dimethyl phosphorodithioa~e3, synergized pyrethrins and Cuprex ~a combination of tetrahyd~ona lene, copper oleate and ac~tone~ the acetone not asser~ed to be active~c Because of increased concern about the overall saety of some o the kno~n ectoparasitic toxicants, the search or ne-ly sae and efective pediculicides has in~ensified recent In addition to killing insects, a good ectoparasitic;de sllould also destroy ova to avoid a resurgence oE the inesta~ion~
surviYing ova may hatch d~ys or ~iee~s after the initial treat-ment. Lac~ing o~icidal activity, a pedlculicide safe to the host usually must be re-applied until control is achie~fed~
~0 It has no-~ been found that those higher alcohols which have a logarithm of their partition coe~-Eicient bet~een n-octan and water of at least 0.61 exhibit pediculicidal andJor o~icidal acti~ity. These alcohols are kno~n materials and have been in-corporated into many pharmaceutical and costmetic prep~rationS.
~or example, ce~yl alcohol constitutes 15% of a published hair groom gel and 61~ of a floatlng bath oil, and lauryl or ~socetyl or dodecyl alcohol constitute about 30~ of a ~ineral oil gel.
~
1~333~0 Cetyl alcohol and lauryl alcohol are also listed und~r the United States Food ~ Drug Administration's approved Synthetic Flavor Substituents and ~djuvants list (21 CFR 1.1.1164). Cetyl alcohol has been used in compositions applied to the skin tU.S.
3,226,295 and 3,943,234) and lauryl alco.hol deTivatives have been used in parasiticides (U.S. 2,Q3~,093).
It is the object of this invention to provide nel~, safe and effective toxicants for lice and their ova, and ~ites. This and other objects of the invention will become apparent to those skilled in the art from the following detailed description.
SU~I~RY OF T~IE I~NENTION
This invention relates to ectoparasiticidal to~icants and a method of controlling ectoparasites. ~lore particularly, the invention relates to the use of certain higher alcohols as toxicants for lice and/or their ova and to toxicant com-postions containing such higher alcohols.
DESCRIPTION OF T~IE PREFERRED E~IBODIhIENTS
.
The toxicants of the instant invention are monohydric alcohols, ROH, in which R is a substituted or unsubstituted alkyl group. The substituting moieties can be aryl, a~yloxy halogen or the like. The R groups generally contain a~ least 4 carbon atoms and the ma~;mum number o~ carbon atoms is not restricted but is generally 24 or less. It has been found -that in order that the alcohols exhibit satisfactory pediculi-cidal and/or ovicidal activity, the logarithm of the partition coefficient (hereinafter log P) for the compound between n-octanol and water must be at lcast 0.61. Log P values can be obtained by consultin~ Leo et al, Chemical Revie~., 71, 525 (1971) or calculated by the ~ethod therein des-cribed. I~.~en pediculicidal activity is desired, it is pre-ferred that the alcohols be unsubstitutea alkyl alcohols havin~
log P values o~ 1.16-7.13. When ovicidal activity is desired,
i~333~V
BAC~G~OUND. 0~: THE INVENTION
~ . . . . .
There are only a relatively few pediculicides whlch are commercially a~ailable *oday. The most popular pediculicidal -toxicants ar~ Lindane (gamma ~enzene hexachloride)~ alathion . .
- [~S-1,2-dicarbethoxyethyl)-O,O-dimethyl phosphorodithioa~e3, synergized pyrethrins and Cuprex ~a combination of tetrahyd~ona lene, copper oleate and ac~tone~ the acetone not asser~ed to be active~c Because of increased concern about the overall saety of some o the kno~n ectoparasitic toxicants, the search or ne-ly sae and efective pediculicides has in~ensified recent In addition to killing insects, a good ectoparasitic;de sllould also destroy ova to avoid a resurgence oE the inesta~ion~
surviYing ova may hatch d~ys or ~iee~s after the initial treat-ment. Lac~ing o~icidal activity, a pedlculicide safe to the host usually must be re-applied until control is achie~fed~
~0 It has no-~ been found that those higher alcohols which have a logarithm of their partition coe~-Eicient bet~een n-octan and water of at least 0.61 exhibit pediculicidal andJor o~icidal acti~ity. These alcohols are kno~n materials and have been in-corporated into many pharmaceutical and costmetic prep~rationS.
~or example, ce~yl alcohol constitutes 15% of a published hair groom gel and 61~ of a floatlng bath oil, and lauryl or ~socetyl or dodecyl alcohol constitute about 30~ of a ~ineral oil gel.
~
1~333~0 Cetyl alcohol and lauryl alcohol are also listed und~r the United States Food ~ Drug Administration's approved Synthetic Flavor Substituents and ~djuvants list (21 CFR 1.1.1164). Cetyl alcohol has been used in compositions applied to the skin tU.S.
3,226,295 and 3,943,234) and lauryl alco.hol deTivatives have been used in parasiticides (U.S. 2,Q3~,093).
It is the object of this invention to provide nel~, safe and effective toxicants for lice and their ova, and ~ites. This and other objects of the invention will become apparent to those skilled in the art from the following detailed description.
SU~I~RY OF T~IE I~NENTION
This invention relates to ectoparasiticidal to~icants and a method of controlling ectoparasites. ~lore particularly, the invention relates to the use of certain higher alcohols as toxicants for lice and/or their ova and to toxicant com-postions containing such higher alcohols.
DESCRIPTION OF T~IE PREFERRED E~IBODIhIENTS
.
The toxicants of the instant invention are monohydric alcohols, ROH, in which R is a substituted or unsubstituted alkyl group. The substituting moieties can be aryl, a~yloxy halogen or the like. The R groups generally contain a~ least 4 carbon atoms and the ma~;mum number o~ carbon atoms is not restricted but is generally 24 or less. It has been found -that in order that the alcohols exhibit satisfactory pediculi-cidal and/or ovicidal activity, the logarithm of the partition coefficient (hereinafter log P) for the compound between n-octanol and water must be at lcast 0.61. Log P values can be obtained by consultin~ Leo et al, Chemical Revie~., 71, 525 (1971) or calculated by the ~ethod therein des-cribed. I~.~en pediculicidal activity is desired, it is pre-ferred that the alcohols be unsubstitutea alkyl alcohols havin~
log P values o~ 1.16-7.13. When ovicidal activity is desired,
2.
:1133390 it is I~reEerr~(l that the alco~lols have log P values of 1.1-7.13 and ~reerably are al~yl alcohols 11avin~ lo~ P
values of 2.3-5.13. Accordingly, when both pediculicidal an-l ovicidal activity is desire~l, it is preferred to employ an unsubstituted alkyl alcohol having log P values of 2.13-5.1.
Typical of the monohydric alcohols which can be employed in this invention are n-butanol, sec-butanol, iso-butanol ~but not tert-butanol), iso-pentanol, n-pentanol, n-hexanol, n-octanol, n-decanol, n-dodecanol, hexadecyl alcollol, oleyl alcohol, benzyl alcohol, 2-phenoxyethanol~ cyclohexanol~
4-chlorobutanol, 2-phenylethanol, and the li~e.
One or ~ore of the toxic alcohols of the present invention can be incorporated into an active toxicant com-position which can be in the form of a liquid~ powder, lotion, cream, gel, aerosol spray, or foam as the result of formulation with inert pharmaceutically acceptable carriers by procedures well known in the art. Any pharmaceuticall~ acceptable carrier, whether aqueous or not aqueous, which is inert to the active ingredient can be employed. By inert is meant that the carrier does not have a substantial detrimental effect on the pediculi-cidal or ovicidal toxicant activity of -the active ingredient.
The active alcohol is incorporated into the toxicant com-positlon used to treat the substrate ~human or animal) in need o such treatment, believed to be in need of such treatment, or desired to be prophylactically protected in an effective toxicant amount By such amount is meant the amount which will cause at least 75% of the ectoparasites e~posed in the two minute immersion tests described below to die within 24 hours in the case of lice and within 2 weeks in the case of the ova. Tlle minimum con-centration of alcohol in the composition re~uired to provide ~11333go an e ~fective tox;c ar,loun-t vclries considera~ly depending on the particular alcohol, the particular inert pharmaceutically acceptable carrier being employecl and any other in~redients ~;hich are present. Thus, in one case a 10% concentration may suffice, while in other cases, concentrations as high as 30 to 40~ may be required to obtain an effective toxic dose. The alcohols can also be employed as an adjuvant toxicant in a preparation which otherwise exhibits pediculicidal and/or ovicidal activity.
In such preparations, the term "effective toxic dose" means tllat amount which ~îll increase the mortality rate by about 20~
in the standard i~mersion test.
The t~o minute i~mersion test referred to above is carried out as follows:
Pediculicidal activity: A 50 ml beaker is filled ~ith tap ~ater and allowed to come to room temperature (about 24C).
Ten young adult male and ten young adult female lice (Pediculus humallus corporis) of the same age group and from the same stock colony are placed on a 2x2 cm coarse mesh-patch. The sample to be 'tested, maintained at room temperature, is shakell until homogeneous and placed into a 50 ml beaker. The mesh patch is placed into the sample immediately af~er pouring, allowed to submerge, and after t~o minutes is removed and immediately plunged into the beaker containing the tap water. The patch is vigorou51y agitated every ten seconds and after one minute,the patch is removed and placed on paper toweling. The lice are then transferred to a 4x4 cm black corduroy cloth patcll and this point of time is con-sidered zero 110UrS. Thereafter, the'corduroy patch is placed in a petri dish ~hich is covered and stored in a 30C holding chamber.
Ovicidal activity: 15 adult, 5 to 10 day old, female lice (Pediculus humanus corporis) are placed Oll a 2x2 cm nylon S]l patC}l ~'}l;Ch is placed in a petri dish, covered and main-tained in an incubator at 30C for 24 hours. The adult lice are then removed and the numbsr of plump, viable eggs and shriveled, non-fertile eggs on the patch are recorded. The sample to be tested, mailltained at room temperature, is shaken until homogeneous and poured into a 50 ml beaker. I~mediately after the pouring, the mesh patch is placed into the beaker, allo~ed to submerge, and after t~o minutes is removed and immediately plunged into a 50 ml beaker containing tap ~ater at room temperature (about 24C). The patch is vigorously agi~ated every ten seconds and after one minute, the p~tch is re~oved and placed on paper toweling for one minute. The patch is then placed in a petri dish WhiC}l is covered and stored in the 30~C
incubator. Fourteen days following treatment, the number of hatched eggs and the number of shriveled or unhatched eggs is noted. I
In hoth the pediculicidal and ovicidal t~o minute immersion tests,controls are run in identical manners to that described with room temperature ~24C~ tap ~ater substituted for the sample to be tested. The results of the tests reported are net results.
In the following tables i and 2, the results of pediculi-cidal and ovicidal testing, respectively, for various alcohols of this invention and other alcohols are set fortll. The alcohols were tested in undiluted form tlO0% alcohol), as a 25~ solution in water, and in a solution containing 15% of the alcohol, 25%
L~S
isopropanol and 60~ r- ("15/25/G0"~. The results are set forth in terms of percent mortality.
`~` 113339~
Table 1 - Pediculicidal Rating 100~ 25%
Alcohol Log P AlcoholSolution lS/25/60 Methanol.-0.66 0 0 Ethanol -0.32 45 . 0 isQ-Propanol-0.12 65 0 0 n-Propanol0.34 70 0 o t~rt-Butanol0.37 80 O O
sec-Butanol0.61 95 0 35 iso-Butanol0.65 95 40 0 n-Butanol 0.88 100 20 . 0 Benzyl Alcohol 1.10 90 0 5 iso-Pentanol1.16 100 55 80 2-Phenoxy-ethanol1.16 100 5 5 Cyclohexanol1.23 100 20 A-Chloro-butanol1O27 100 0 20 2-Phenyl- -ethanolla 36 100 0 80 n-Pentanol1.40 100 10 75 n-Hexanol 2.03 100 5 85 n-Octanol 3.15 100 10 85 n-Decanol 4.15 100 20 gs n-Dodecanol5.13 100 10 ioo Hexadecyl Alcohol~ 7.13 100 40 go Oleyl Alcohol 7.47 100 0 40 .
Table II
Ovicidal Rat~
Alcohol Log p lOO~ Alcohol25~ Solution15/25/60 _ ~lethanol -0.66 4 27 0 Ethanol -0.32 4 7 - 13 iso-Propanol -0.12 . 1 O
n-Propanol 0.34 27 23 tert-Butanol 0.37 16 17 O
sec-Butanol 0.61 10 46 32 iso-Butanol 0.65 0 58 2 N-Butanol 0.88 48 17 2 ~enzyl Alcohol1.10 100 100 . 29 iso-Pentanol 1.16 100 52 - O
2-Phenoxyethanol 1.16 100 100 100 Cyclohexanol 1.23 100 57 4-Chlorobutanol1.27 100 100 100 2-Phenylethanol1.36 100 ~ 100 3~
n-Pentanol 1.40 100 67 35 n-Hexanol 2.03 100 100 100 n-Octanol 3.15 100 . 100 100 n-Decanol 4.15 100 100 100 n-Dodecanol 5.13 100 100 100 Hexadecyl Alcohol'7.13100 75 29 Oleyl Alcohol 7~47 l4 0 20 7 ~ ... ..
113339(~
The miticidal activity of the instant toxicants was determined as follo~s. Into a one cubic foot chamber, held at room temperature, is placed a covered microscope depression slide containing ten adult mixed sex mites,P~roptes equi var. cuniculi.
The slide is positioned at a distance of ten inches horizontall~ -and four inches below the activator of a mechanical spray device and uncovered. The mechanical p~mp spray de~ice delivers 50 micrograms of sample per depression of the activator.
The sample to be tested, maintained at rcom tempera*ure, is shaken until homogenous and placed in the mechanical pump spray device. The primed activ~tor is depressed twice, releasing 100 micrograms of spray mist into the closed chamber. The mist is allowed to settle and the slide containing the mites is removed and covered. This point of time is considered zero hours. The covered slide `is then held at room temperature for 24 hours. Microscopic observations are noted at 0, l,
:1133390 it is I~reEerr~(l that the alco~lols have log P values of 1.1-7.13 and ~reerably are al~yl alcohols 11avin~ lo~ P
values of 2.3-5.13. Accordingly, when both pediculicidal an-l ovicidal activity is desire~l, it is preferred to employ an unsubstituted alkyl alcohol having log P values of 2.13-5.1.
Typical of the monohydric alcohols which can be employed in this invention are n-butanol, sec-butanol, iso-butanol ~but not tert-butanol), iso-pentanol, n-pentanol, n-hexanol, n-octanol, n-decanol, n-dodecanol, hexadecyl alcollol, oleyl alcohol, benzyl alcohol, 2-phenoxyethanol~ cyclohexanol~
4-chlorobutanol, 2-phenylethanol, and the li~e.
One or ~ore of the toxic alcohols of the present invention can be incorporated into an active toxicant com-position which can be in the form of a liquid~ powder, lotion, cream, gel, aerosol spray, or foam as the result of formulation with inert pharmaceutically acceptable carriers by procedures well known in the art. Any pharmaceuticall~ acceptable carrier, whether aqueous or not aqueous, which is inert to the active ingredient can be employed. By inert is meant that the carrier does not have a substantial detrimental effect on the pediculi-cidal or ovicidal toxicant activity of -the active ingredient.
The active alcohol is incorporated into the toxicant com-positlon used to treat the substrate ~human or animal) in need o such treatment, believed to be in need of such treatment, or desired to be prophylactically protected in an effective toxicant amount By such amount is meant the amount which will cause at least 75% of the ectoparasites e~posed in the two minute immersion tests described below to die within 24 hours in the case of lice and within 2 weeks in the case of the ova. Tlle minimum con-centration of alcohol in the composition re~uired to provide ~11333go an e ~fective tox;c ar,loun-t vclries considera~ly depending on the particular alcohol, the particular inert pharmaceutically acceptable carrier being employecl and any other in~redients ~;hich are present. Thus, in one case a 10% concentration may suffice, while in other cases, concentrations as high as 30 to 40~ may be required to obtain an effective toxic dose. The alcohols can also be employed as an adjuvant toxicant in a preparation which otherwise exhibits pediculicidal and/or ovicidal activity.
In such preparations, the term "effective toxic dose" means tllat amount which ~îll increase the mortality rate by about 20~
in the standard i~mersion test.
The t~o minute i~mersion test referred to above is carried out as follows:
Pediculicidal activity: A 50 ml beaker is filled ~ith tap ~ater and allowed to come to room temperature (about 24C).
Ten young adult male and ten young adult female lice (Pediculus humallus corporis) of the same age group and from the same stock colony are placed on a 2x2 cm coarse mesh-patch. The sample to be 'tested, maintained at room temperature, is shakell until homogeneous and placed into a 50 ml beaker. The mesh patch is placed into the sample immediately af~er pouring, allowed to submerge, and after t~o minutes is removed and immediately plunged into the beaker containing the tap water. The patch is vigorou51y agitated every ten seconds and after one minute,the patch is removed and placed on paper toweling. The lice are then transferred to a 4x4 cm black corduroy cloth patcll and this point of time is con-sidered zero 110UrS. Thereafter, the'corduroy patch is placed in a petri dish ~hich is covered and stored in a 30C holding chamber.
Ovicidal activity: 15 adult, 5 to 10 day old, female lice (Pediculus humanus corporis) are placed Oll a 2x2 cm nylon S]l patC}l ~'}l;Ch is placed in a petri dish, covered and main-tained in an incubator at 30C for 24 hours. The adult lice are then removed and the numbsr of plump, viable eggs and shriveled, non-fertile eggs on the patch are recorded. The sample to be tested, mailltained at room temperature, is shaken until homogeneous and poured into a 50 ml beaker. I~mediately after the pouring, the mesh patch is placed into the beaker, allo~ed to submerge, and after t~o minutes is removed and immediately plunged into a 50 ml beaker containing tap ~ater at room temperature (about 24C). The patch is vigorously agi~ated every ten seconds and after one minute, the p~tch is re~oved and placed on paper toweling for one minute. The patch is then placed in a petri dish WhiC}l is covered and stored in the 30~C
incubator. Fourteen days following treatment, the number of hatched eggs and the number of shriveled or unhatched eggs is noted. I
In hoth the pediculicidal and ovicidal t~o minute immersion tests,controls are run in identical manners to that described with room temperature ~24C~ tap ~ater substituted for the sample to be tested. The results of the tests reported are net results.
In the following tables i and 2, the results of pediculi-cidal and ovicidal testing, respectively, for various alcohols of this invention and other alcohols are set fortll. The alcohols were tested in undiluted form tlO0% alcohol), as a 25~ solution in water, and in a solution containing 15% of the alcohol, 25%
L~S
isopropanol and 60~ r- ("15/25/G0"~. The results are set forth in terms of percent mortality.
`~` 113339~
Table 1 - Pediculicidal Rating 100~ 25%
Alcohol Log P AlcoholSolution lS/25/60 Methanol.-0.66 0 0 Ethanol -0.32 45 . 0 isQ-Propanol-0.12 65 0 0 n-Propanol0.34 70 0 o t~rt-Butanol0.37 80 O O
sec-Butanol0.61 95 0 35 iso-Butanol0.65 95 40 0 n-Butanol 0.88 100 20 . 0 Benzyl Alcohol 1.10 90 0 5 iso-Pentanol1.16 100 55 80 2-Phenoxy-ethanol1.16 100 5 5 Cyclohexanol1.23 100 20 A-Chloro-butanol1O27 100 0 20 2-Phenyl- -ethanolla 36 100 0 80 n-Pentanol1.40 100 10 75 n-Hexanol 2.03 100 5 85 n-Octanol 3.15 100 10 85 n-Decanol 4.15 100 20 gs n-Dodecanol5.13 100 10 ioo Hexadecyl Alcohol~ 7.13 100 40 go Oleyl Alcohol 7.47 100 0 40 .
Table II
Ovicidal Rat~
Alcohol Log p lOO~ Alcohol25~ Solution15/25/60 _ ~lethanol -0.66 4 27 0 Ethanol -0.32 4 7 - 13 iso-Propanol -0.12 . 1 O
n-Propanol 0.34 27 23 tert-Butanol 0.37 16 17 O
sec-Butanol 0.61 10 46 32 iso-Butanol 0.65 0 58 2 N-Butanol 0.88 48 17 2 ~enzyl Alcohol1.10 100 100 . 29 iso-Pentanol 1.16 100 52 - O
2-Phenoxyethanol 1.16 100 100 100 Cyclohexanol 1.23 100 57 4-Chlorobutanol1.27 100 100 100 2-Phenylethanol1.36 100 ~ 100 3~
n-Pentanol 1.40 100 67 35 n-Hexanol 2.03 100 100 100 n-Octanol 3.15 100 . 100 100 n-Decanol 4.15 100 100 100 n-Dodecanol 5.13 100 100 100 Hexadecyl Alcohol'7.13100 75 29 Oleyl Alcohol 7~47 l4 0 20 7 ~ ... ..
113339(~
The miticidal activity of the instant toxicants was determined as follo~s. Into a one cubic foot chamber, held at room temperature, is placed a covered microscope depression slide containing ten adult mixed sex mites,P~roptes equi var. cuniculi.
The slide is positioned at a distance of ten inches horizontall~ -and four inches below the activator of a mechanical spray device and uncovered. The mechanical p~mp spray de~ice delivers 50 micrograms of sample per depression of the activator.
The sample to be tested, maintained at rcom tempera*ure, is shaken until homogenous and placed in the mechanical pump spray device. The primed activ~tor is depressed twice, releasing 100 micrograms of spray mist into the closed chamber. The mist is allowed to settle and the slide containing the mites is removed and covered. This point of time is considered zero hours. The covered slide `is then held at room temperature for 24 hours. Microscopic observations are noted at 0, l,
3, and 24 hours post treatment. Controls are run in an identical ~anner as that described using water or the diluting agent ?
and net mortality results are reported.
TABLE III
~liticidal Rating 50~ Solution in Alcohol log P 100~ Alcohol Isopro~anol iso-Propanol -0.12* 0 sec-Butanol 0.61 50 n-Butanol 0.88 100 Benzyl Alcohol 1.10 100 Cyclohexanol 1.23 - lO0 2-Phenylethanol 1.36 lO0 n-Pentanol 1.40 100 n-~lexanol 2.03 lO0 ~lexadecyl Alcohol~ 7.13* lO0 Oleyl Alcohol 7.47* 30 ,, .
`
:~33390 Tlle log P values sct forth in the foregoing tables I, II
and III are those set forth in the aforementioned Leo et al article except for the values starred ~hich were calculated using standard methods. The log P value for hexadecyl alcohol is a calculated value and the actual figure is dependent on the degree of branching o the alkyl moiety.
As noted above, various end use formulations can be prepared. Some typical formulations are set forth below and the amoun~s recited are percentages by weight:
Clear calorless liquid suitable for mechanical spray application or inunction Isopropyl alcohol - 65 ~lexadecyl alcohol 15 IYater 20 Clear s}iampoo Isopropyl alcohol 25 n-Dodecanol lS
Triethanolamine lauryl sul-Eate 20 Water 40 Lotion Isopropyl alcohol 25 Hexadecyl alcohol 15 Carbo~ypolymethylene 0.1 Triethanolamine 0.1 -Water 59.8 g 1~33390 cream Isopropyl alcohol 25.0 Isopentanol . 15.0 Glyceryl monostearate 22.5 Sorbitan monostearate 1.5 . - Polysorbate 60 3.5 Xanthan gum 0.2 : Water 32.3 Quick Breaking Aerosol Foam Mono and diglycerides from the glycerides o~ edible fats 8 n-Octanol 15 Isopropanol 25 Glycerine 3 : Isobutane 8 Water 41 Powder -~' 4-chlorobutanol 10 - Talc . 9O
Stick Sodium stearate . 8.0 Sorbitol 3.5 Isopropanol 25.0 Ethanol 39.0 n_Decanol 15.0 Water 9 5 . .
.
~133390 .
Gel Carboxypolymethylene 1.5 Isopropyl alcohol . 25.0
and net mortality results are reported.
TABLE III
~liticidal Rating 50~ Solution in Alcohol log P 100~ Alcohol Isopro~anol iso-Propanol -0.12* 0 sec-Butanol 0.61 50 n-Butanol 0.88 100 Benzyl Alcohol 1.10 100 Cyclohexanol 1.23 - lO0 2-Phenylethanol 1.36 lO0 n-Pentanol 1.40 100 n-~lexanol 2.03 lO0 ~lexadecyl Alcohol~ 7.13* lO0 Oleyl Alcohol 7.47* 30 ,, .
`
:~33390 Tlle log P values sct forth in the foregoing tables I, II
and III are those set forth in the aforementioned Leo et al article except for the values starred ~hich were calculated using standard methods. The log P value for hexadecyl alcohol is a calculated value and the actual figure is dependent on the degree of branching o the alkyl moiety.
As noted above, various end use formulations can be prepared. Some typical formulations are set forth below and the amoun~s recited are percentages by weight:
Clear calorless liquid suitable for mechanical spray application or inunction Isopropyl alcohol - 65 ~lexadecyl alcohol 15 IYater 20 Clear s}iampoo Isopropyl alcohol 25 n-Dodecanol lS
Triethanolamine lauryl sul-Eate 20 Water 40 Lotion Isopropyl alcohol 25 Hexadecyl alcohol 15 Carbo~ypolymethylene 0.1 Triethanolamine 0.1 -Water 59.8 g 1~33390 cream Isopropyl alcohol 25.0 Isopentanol . 15.0 Glyceryl monostearate 22.5 Sorbitan monostearate 1.5 . - Polysorbate 60 3.5 Xanthan gum 0.2 : Water 32.3 Quick Breaking Aerosol Foam Mono and diglycerides from the glycerides o~ edible fats 8 n-Octanol 15 Isopropanol 25 Glycerine 3 : Isobutane 8 Water 41 Powder -~' 4-chlorobutanol 10 - Talc . 9O
Stick Sodium stearate . 8.0 Sorbitol 3.5 Isopropanol 25.0 Ethanol 39.0 n_Decanol 15.0 Water 9 5 . .
.
~133390 .
Gel Carboxypolymethylene 1.5 Isopropyl alcohol . 25.0
4-Chlorobutanol 10.0 Polysorbate ~0 4.0 Triethanolamine 3.0 Water 56.5 Various changes and modifications can be made in the instant invention without departing from the spirit and scope thereof. The various embodiments set forth herein were for the purpose of further illustrating the invention and were not intended to limit it. Throughout this specifi-: cation and claims, all parts and percentages have been by weight and all temperatures in degrees Centigrade unless otherwise indicated.
.... .
.
r
.... .
.
r
Claims (19)
1. A method of controlling mites which comprises applying to a human or animal host believed in need of such control, an effective toxic amount of at least one mono-hydric alcohol whose logarithm of the partition coefficient between n-octanol and water (log P) is at least 0.61.
2. The method of claim 1 whereins aid alcohol has a log P of 1.1-7.13.
3. The method of claim 2 wherein said alcohol is an alkanol having a log P of 2.3-5.13.
4. The method of claim 3 wherein said alcohol is selected from the group consisting of octanol, decanol, dodecanol and hexadecyl alcohol.
5. The method of claim 1 wherein said alcohol is employed in combination with an inert pharmaceutically accept-able carrier.
6. The method of claim 5 wherein said carrier is aqueous.
7. A method of controlling lice comprising applying to a human or animal host in need of such control, an effective toxic amount of a monohydric alcohol selected from the group consisting of iso-pentanol, 2-phenyl-ethanol, n-pentanol, n-hexanol, n-octanol and hexadecyl alcohol in an inert pharmaceutically acceptable carrier.
8. The method of claim 7 wherein said carrier is aqueous.
9. The method of claim 8 wherein said carrier contains isopropanol.
10. The method of claim 9 wherein said alcohol is iso-pentanol.
11. The method of claim 8 wherein said alcohol is 2-phenyl-ethanol.
12. The method of claim 9 wherein said alcohol is n-pentanol.
13. The method of claim 9 wherein said alcohol is n-octanol.
14. The method of claim 9 wherein said alcohol is hexadecyl alcohol.
15. A method of controlling Pediculus ova which comrpises applying to a human or animal host in need of such control an effective toxic amount of a monohydric alcohol selected from the group consisting of n-hexanol, dodecanol and hexadecyl alcohol in an inert pharmaceutically acceptable carrier.
16. The method of claim 15 wherein said carrier is aqueous.
17. The method of claim 15 wherein said alcohol is n-hexanol.
18. The method of claim 15 wherein said alcohol is dodecanol.
19. The method of claim 15 wherein said alcohol is hexadecyl alcohol.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80201477A | 1977-05-31 | 1977-05-31 | |
| US802,014 | 1977-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1133390A true CA1133390A (en) | 1982-10-12 |
Family
ID=25182620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA304,411A Expired CA1133390A (en) | 1977-05-31 | 1978-05-30 | Higher alcohol toxicants |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS545028A (en) |
| AU (1) | AU519808B2 (en) |
| BE (1) | BE867613A (en) |
| CA (1) | CA1133390A (en) |
| CH (1) | CH633163A5 (en) |
| DE (1) | DE2823594A1 (en) |
| FR (1) | FR2392602B1 (en) |
| GB (2) | GB1604857A (en) |
| PH (1) | PH16721A (en) |
| SE (1) | SE443492B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5675403A (en) * | 1979-11-24 | 1981-06-22 | King Kagaku Kk | Rapid-acting agent for killing slug and snail |
| JPH07103001B2 (en) * | 1989-10-19 | 1995-11-08 | 高砂香料工業株式会社 | Acaricide |
| ES2096648T3 (en) * | 1990-04-18 | 1997-03-16 | Procter & Gamble | COMPOSITIONS FOR TREATMENT AGAINST LICE. |
| WO1991015953A1 (en) * | 1990-04-18 | 1991-10-31 | The Procter & Gamble Company | Anti-lice treatment compositions |
| US5288483A (en) * | 1990-04-18 | 1994-02-22 | The Procter & Gamble Company | Anti-lice treatment compositions |
| CA2130375C (en) * | 1993-10-01 | 2004-08-17 | Lynn Sue James | Insecticide and insect repellant compositions |
| AP2007003968A0 (en) * | 2004-10-01 | 2007-04-30 | Prometic Biosciences Inc | Medium-chain length fatty alcohols as stimulators of hematopoiesis |
| US20060140995A1 (en) * | 2004-12-23 | 2006-06-29 | Precopio Michael J | Methods for treating ectoparasite infections on the mammalian body |
| JP2012031169A (en) * | 2010-07-09 | 2012-02-16 | Osaka Seiyaku:Kk | Lice eliminator |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE237408C (en) * | ||||
| DE502204C (en) * | 1926-10-12 | 1930-07-17 | I G Farbenindustrie Akt Ges | Means for combating pests |
| US2030093A (en) * | 1932-12-29 | 1936-02-11 | Grasselli Chemical Co | Parasiticides |
| DE1025668B (en) * | 1954-04-20 | 1958-03-06 | Rohm & Haas | Pest repellants |
| US3226295A (en) * | 1960-02-08 | 1965-12-28 | Carlos C Goetz | Method of making cetyl alcohol emulsions |
| US3287213A (en) * | 1965-06-30 | 1966-11-22 | Janssen Pharmaceutica Nv | Method of combatting arachnids and fungi |
| US3634264A (en) * | 1967-11-02 | 1972-01-11 | Univ California | Method and composition for cleansing hair of animals |
| DE1961152A1 (en) * | 1968-12-09 | 1970-06-25 | Kolmar Laboratories | Bactericidal and fungicidal skin preparation - with middle chain alcohols |
| JPS4896719A (en) * | 1972-03-23 | 1973-12-10 | ||
| US3943234A (en) * | 1973-08-09 | 1976-03-09 | The Procter & Gamble Company | Acidic emollient liquid detergent composition |
| US3966969A (en) * | 1975-03-06 | 1976-06-29 | Zoecon Corporation | Spider mite control |
| US4147800A (en) * | 1977-01-17 | 1979-04-03 | Block Drug Company, Inc. | Pediculicidal toxicants |
-
1977
- 1977-10-18 GB GB32139/77A patent/GB1604857A/en not_active Expired
- 1977-10-18 GB GB22691/80A patent/GB1605128A/en not_active Expired
-
1978
- 1978-05-18 PH PH21154A patent/PH16721A/en unknown
- 1978-05-24 AU AU36431/78A patent/AU519808B2/en not_active Expired
- 1978-05-26 CH CH574778A patent/CH633163A5/en not_active IP Right Cessation
- 1978-05-30 DE DE19782823594 patent/DE2823594A1/en active Granted
- 1978-05-30 FR FR7816049A patent/FR2392602B1/en not_active Expired
- 1978-05-30 BE BE188154A patent/BE867613A/en not_active IP Right Cessation
- 1978-05-30 CA CA304,411A patent/CA1133390A/en not_active Expired
- 1978-05-31 JP JP6446078A patent/JPS545028A/en active Granted
- 1978-07-25 SE SE7808134A patent/SE443492B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2823594C2 (en) | 1991-06-20 |
| GB1604857A (en) | 1981-12-16 |
| AU3643178A (en) | 1979-11-29 |
| PH16721A (en) | 1984-01-25 |
| JPS545028A (en) | 1979-01-16 |
| JPH0120124B2 (en) | 1989-04-14 |
| CH633163A5 (en) | 1982-11-30 |
| BE867613A (en) | 1978-11-30 |
| DE2823594A1 (en) | 1978-12-14 |
| SE443492B (en) | 1986-03-03 |
| SE7808134L (en) | 1980-01-26 |
| AU519808B2 (en) | 1981-12-24 |
| FR2392602A1 (en) | 1978-12-29 |
| FR2392602B1 (en) | 1985-07-12 |
| GB1605128A (en) | 1981-12-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4368207A (en) | Higher alcohol toxicants effective against insects | |
| US4147800A (en) | Pediculicidal toxicants | |
| CA1108529A (en) | Siloxane toxicants | |
| CA1133390A (en) | Higher alcohol toxicants | |
| US4179504A (en) | Alkyl amine oxide toxicants | |
| GB1604859A (en) | Ectoparasiticidal toxicants | |
| US4215116A (en) | Propoxylate toxicants | |
| CA1113855A (en) | Antipruritic ectoparasiticide | |
| JPS61268602A (en) | Novel composition and method for controlling cockroach | |
| US4238499A (en) | Method of killing ectoparasites with imidazoline and imidazolium toxicants | |
| US4497831A (en) | Polyoxyethylene derivatives as antipruritic ectoparasiticide | |
| US4372977A (en) | Polyoxethylene derivatives as antipruritic ectoparasiticide | |
| CA1109789A (en) | Polyol toxicants | |
| US4263321A (en) | Alkanol amide toxicants | |
| CA1103150A (en) | Glycine toxicants | |
| US4584319A (en) | Polyoxyethylene derivatives as antipruritic ectoparasiticide | |
| US3030268A (en) | Process and composition for attracting and combatting insects, in particular the mediterranean fruit fly | |
| US4126700A (en) | Aminopropionic-acids as ectoparasiticides | |
| CA1125655A (en) | Amidoamine toxicants | |
| US4491576A (en) | Polyoxyethylene derivatives as antipruritic ectoparasiticide | |
| Young et al. | Effects of several insect growth regulators on egg hatch and subsequent development in the cabbage maggot Delia radicum (L.)(Diptera: Anthomyiidae) | |
| EP0147947A1 (en) | Insecticidal composition | |
| RU2214093C2 (en) | Preparation for protection against keratophages | |
| RU2163439C1 (en) | Insecticide preparation | |
| JPS5948807B2 (en) | Acaricide, insecticidal composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |