AU615467B2 - Potentiated insect repellent composition and method - Google Patents
Potentiated insect repellent composition and method Download PDFInfo
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- AU615467B2 AU615467B2 AU21424/88A AU2142488A AU615467B2 AU 615467 B2 AU615467 B2 AU 615467B2 AU 21424/88 A AU21424/88 A AU 21424/88A AU 2142488 A AU2142488 A AU 2142488A AU 615467 B2 AU615467 B2 AU 615467B2
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- cic
- toluamide
- lactone
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
W~:il; COMMONWEALTH OF AUSTRALIA 6 546 7 FORM PATENTS ACT 1952 C O M P T, .R T T PRDV T 7 T r A T r r 0 M P E T E S P E r T V FOR OFFICE USE: Class Int.Class Application Number: Lodged: Complete Specification Lodged: Accepted: Published: Priority: elated Art: Name of Applicant: Address of Applicant: Actual Inventor: ANGUS CHEMICAL COMPANY 2211 Sanders Road, Northbrook, Illinois, 60061, United States of America FREDERICK COULSTON and FRIEDRICH W.A.G.K.
KORTE
Address for Service: SHELSTON WATERS, 55 Clarence Street, Sydney complete Specification for the Invention entitled: "POTENTIATED INSECT REPELLENT COMPOSITION AND METHOD" The following statement is a full description of this invention, including the best method of performing it known to me/us:- -1- Patent of Addition of 42891/85 (573,001) dated 27th May, 1985 -L 1 The present invention relates to an improvement in potentiated insect repellent compositions comprising Deet N-diethyl-meta-toluamide), and a class of bicyclic lactones having insect repellent activity, as described in Australian patent No. 573,001, herein referred to as the main invention.
Certain substances which enhance or otherwise augment the repellent activity of Deet are well known.
It was pointed out in U.S. 4,427,700 that Deet, by itself, is primarily effective used only against mosquitoes, as it (Deet) is known to possess little or only mediocre repellent activity against a variety of other commonly-encountered bothersome insects, black flies (col. 1, 11. 36-38).
SBordenca et al., U.S. Reissue 29,829 discloses Scompositions containing secondary and tertiary hydroxylamines as insect repellents.
Croxall et al. U.S. 2,459,684 relates to lactones formed from half esters of substituted tetrahydrophthalic acid which are said to be useful as insecticidal toxicants and repellents. These compounds however differ greatly in structure from the present bicyclic lactones.
It is therefore an object of this invention to provide improved potentiated insect repellent compositions which S are effective repellents against a wide variety of insects, including ants, fleas, flies, mosquitoes, and the like.
S
t A potentiated insect repellent composition, as the term is used herein to define this invention and the main invention, means a repellent composition which produces a result substantially in excess of that which reasonably could be expected or predicted from the known effect of the components either alone or additively.
The combination of Deet with the Iridomyrmecin derivatives disclosed herein provides such a potentiated effect. Whie we do not wish to be committed to a specific -2r i theory of action, it appears that there is a cooperative effect over a rather wide ratio of either compound to the other, as more clearly seen hereinafter. Whatever the theory, the resulting composition is a strong, effective, relatively less expensive and relatively less toxic repellent composition than either one taken alone. The result was unpredictable and surprising.
In accordance with the foregoing objects, the potentiated insect repellent composition of the present invention will now be summarized. The composition comprises Deet and a compound of the formula:
R'
R'
-(CH
2 0
(CH
2 )y 0 R R' or the corresponding unsaturated compound thereof having the formula a i -r, wherein R, each are lower alkyl
C
1
-C
4 or hydrogen; 3 ~i wherein y is an integer from 1-3, and x and z each are 0 or 1, with the proviso that y is 1 or 2 when x is 1.
Preferably, R, and each are hydrogen or methyl. Also preferably, the composition further comprises a carrier.
The foregoing, as well as other objects, features and advantages of the present invention will become more readily understood upon reading the following detailed description of the preferred embodiments.
DETAILED DESCRIPTION OF THE PREFERRED COMPOSITIONS Considering the invention in one way, preferably, the repellent compositions comprises Deet, a carrier, and about 0.025-10 weight percent of bicyclic lactone of the class shown on Table I, based on the total weight of the composition. More preferably, the composition comprises 0.25-5 weight percent of Table I bicyclic lactone, and up to 10 weight percent Deet, in a carrier.
Stating the invention alternatively within the foregoing context, our preferred improved compositions 20 comprise a combination or mixture of a bicyclic lactone e and the toluamide in an amount effective to repel insects, and a carrier, the mixture comprising the ratio the ratio S"of one part by weight of bicyclic lactone to each 0.025 to 10 parts by weight of the toluamide.
Preferably the compositions comprises about one part by weight of bicyclic lactone to each 0.5 to 10 parts by weight of toluamide.
4 Alternatively the composition may comprise about 0.25-10 parts by weight of bicyclic lactone to about 0.25-10 parts by weight of toluamide.
Of course it is possible to add either the lactone or Deet in amounts greater than indicated above. We have noted, however, that at higher concentrations there may be a masking effect of one component on the other so that the potentiation, through present, becomes difficult to observe in a biological test. In such higher concentrations the excess active ingredients may be wasted or unnecessary.
Values of structural variables of the preferred bicyclic lactones, and abbreviations used through this application to refer to such lactones, appear below in Table I: ®C
T
r 4~ 4 a 4 *1 -'pa 'pa a TABLE I Abbreviation compound is Values of Structural x y z R Variables
R'
R"
CIC-2 CIC-3a CIC-4 CIC-6 CIC-7 CIC-8 CIC-9 CIC-21 CIC-22 CIC-23 CIC-24 CIC-26 sat.
sat.
sat.
unsat.
sat.
unsat.
sat.
unsat.
unsat.
sat.
sat.
sat.
sat.
sat.
sat.
sat.
0 0 0 0 0 0 0 0 0 0 0 0 1 1 1.
0
CH
3
CH
3
H
CH
3
H
H
CH
3
H
CH
3
CH
3
CH
3
CH
3
CH
3
CH
3
CH
3
CH
3
CH
3
H
H
H
H
H
H
H
H
H
H
CH
3
H
H
CH
3
H
H
H
H
non.
H
non.
H
non.
non.
H
H
H
H
H
H
CH
3
H
CH
3
H
H
CH
3
H
H
sat. saturated non. nonexistent unsat. unsaturated Somewhat more widely-recognizable names for these compounds are as follows. CIC-2 known as alpha-(2hydroxymethyl-3-methyl-cyclopentyl) propionic acid lactone. Its trivial name is Iridomyrmecin. CIC-3a is known as alpha-(2-hydroxymethyl-cyclohexyl) propionic acid lactone. CIC-4 is known as (2-hydroxymethyl-cyclohexyl) acetic acid lactone. CIC-5 is known as alpha-(2hydroxymethyl-cyclohexylidene) propionic acid lactone.
CIC-6 is known as (2-hydroxymethyl-cyclopentyl) acetic acid lactone. CIC-7 is known as (2-hydroxymethylcyclohexylidene) acetic acid lactone (see, B. Belleau, Canadian Journal of Chemistry, 35, 673 (1957)). CIC-8 is known as alpha-(2-hydroxymethyl-cyclopentyl) propionic n acid lactone. CIC-9 is known as (2-hydroxymethylcyclopentylidene) acetic acid lactone. CIC-O10 is known as alpha-(2-hydroxymethyl-cyclopentylidene) propionic acid riti lactone. CIC-20 is known as alpha-(2-hydroxycyclohexyl) propionic acid lactone. CIC-21 is known as alpha-(2hydroxy-4-methylcyclohexyl) propionic acid lactone.
CIC-22 is known as alpha-(2-hydroxy-3-methylcyclohexyl) propionic acid lactone. CIC-23 is known as alpha-(3hydroxycyclohexyl) propionic acid lactone. CIC-24 is known as alpha-(3-hydroxy-4-methylcyclohexyl) propionic acid lactone. CIC-25 is known as alpha-(3-hydroxy-3methylcyclohexyl) propionic acid lactone. CIC-26 is known as alpha-(2-hydroxycycloheptyl) alpha, alpha-dimethyl propionic acid lactone.
9P .The class of bicyclic lactones shown in Table I,
I
S including methods of synthesis thereof and tests demonstrating the insect repellent activities therof, are discussed and disclosed in the main invention, Australian Patent No. 573,001.
Bicyclic lactones (Table I) of such a class to have effective insect repellent activity. The Table I lactones, and the repellent compositions of the present invention, were effective non-contact repellents, viz., 6the insect is repelled, usually without having made contact with the repellent composition or host.
The nomenclature used in this patent has been used in the literature (including the Tetrahedron article briefly referred to above) and throughout the Chemnical Abstracts up to 1966. After 1967, the Chemical Abstracts generally have used and now use the following names for the underlying CIC chemical skeletal structure, with the noted exception.
CHEMICAL SKELETAL STRUCTURE CHEMICAL ABSTRACTS NAME 00 4A I I I trig (I lIlt I C It I 0a 0 ca0 5,6,7, 7a-Tetrahydrocyclopenta pyran-3 (3.H)-one Hexahydrocyclopenta pyran-3 (lH)-one 1,5,6,7,8, 8a-hexahydro-3H-2benzopyran-3 -one Hexahydro-3-isochromanone (up to 1972), (and after 1972) l1,4,5,6,7,8,8a-Octahydro-3H- 2-benzo--pyran-3 -one It 1111 I I
I
~Ir.e 0 Hexahydro-2 -benzofuranone :0 2-Oxabicyclo [3.3.1] -o nonan-3-one -7 U Hexahydrocyclohepta pyran- 3(1H)-one Example 1 Combinations of CIC-4 Lactone and Deet Various combinations of CIC-4 lactone (2-hydroxymethylcyclohexyl acetic acid lactone) and Deet were applied in a carrier to Rhesus monkeys (Macaca Mulatta).
An application of 1.2 ml of test substance was made with an additional 0.2 ml added for cotton absorbency.
S The area of application on each animal was a circle of approximately 80 cm 2 in area. The test substances were dissolved in Everclear T grain alcohol, one hundred and ninety (190) proof.
Mosquitos used to test repellency were female Aedes aegypti, 5-7 days old. Prior to experimentation on the monkeys, the mosquitos were tested on humans as controls r, and they bit well. Cylindrical containers of clear plastic, with marquisette placed over both ends, were used S to contain the mosquitos. The volume of the containers 3 was about 375 cm 3 The open area of the marquisette-covered ends matches the area of application on the monkey.
Test substances were applied with a cotton swab.
After one hour, testing began. Compounds were tested hourly for the first three hours, then usually on the half hour for longer periods of time. The results are summarized in Table II.
8 TABLE II Monkey Miimi r Compounds Ratio flTr/C./DET Repellency TTP q Total c-oncentration CIC-4
DEET
*1 t~
I
II
r
I
ill *64£ C C
C
C C C C C I C LI C- C I I C I CI I I%~I SI C CIC-4 DEET (1.82%) CIC-4 DEBT 6%) CIC-4 DEET (1.33%) CIC-4 DEET (19a) CIC-4 DEET 1:10 1:4 5.51 5.51 1:2 1:1 1:1 5.51 yi 1 Repellency activity extended to )5 1/2 hours without breakthrough.
Breakthrough is the point at which 2-5 or more mnosquitos landed and started biting, with blood insect.
Example 2 Repellent Activity of CIC-4 and DEET Combinations The active ingredients, CIC-4, DEET, and combinations thereof, were dissolved in ethanol and applied in varying concentrations to the shaved bellies of Rhesus monkeys.
9- 1 ml of the ethanol solution was applied to a circle of 2 approximately 80 cm Mosquitoes (female Aedas aegypti) were brought into j contact with the treated and control areas through a cylindrical vial of the same description as set forth above in Example 1.
Twenty to thirty mosquitoes were placed in the vial to evaluate repellency. Prior to bringing them into contact with the treated areas, the mosquitoes were brought into contact with a shaved, untreated area of the monkey's thigh to ensure the mosquitoes were biting.
A "fresh" vial, one which previously had not been exposed to treated areas, was brought into contact with the treated area for two minute durations at thirty minute intervals. Breakthrough in this Example is defined as the time at which a single bite is observed or multiple oval landings appeared to negate a repellent effect.
The results of this experiment are set forth in Table t III below.
TABLE III Total CIC-4 DEET Breakthourgh Ruin (hrs)- 1 0.25 0.25 2 0.25 0.25 3 0.50 0.25 0.25 4 0.50 0.50 0.50 0.5 6 1.0 1.0 7 1.0 1.0 8 1.0 0.75 0.25 92.0 2.0 2.0 1.75 0.25 11. 4.0 4.0 12 4.0 3.75 0.25 10.0 10 Example 3 Repellent Activity of CIC-7 and DEET Combinations The active ingredients, CIC-7 (2-hydroxymethylcyclohexylidene acetic acid lactone), DEET, and combinations thereof, were applied in varying concentrations to the shaved bellies of Rhest. ,.ionkeys in 1.2 ml of an ethanol solution. The area of application 2 was a circle of approximately 80 cm Mosquitoes (female (Aedas aevypti) were brought into contact with the treated and control areas through a cylindrical vial of the same description as set forth it '10 above in Example 1.
Ten to fifteen mosquitoes were placed in the vial to evaluate repellency. Prior to bringing them into contact with the treated area, the mosquitoes were brought into contact with an untreated area of a control monkey to ensure that the mosquitoes were biting.
A fresh vial was brought into contact with the treated area for two minute durations at 30 minute intervals for the first three hours, hourly for the next three hours, and every half hour until breakthrough occurred. Breakthrough in this Example is defined as the time at which a single bite with multiple landings occurz.
The results of this experiment are set forth in Table IV below.
11 TABLE IV Run 1 2 3 4 6 7 8 9 Total (wti) CIC-7 (wt%)
DEET
(wt%) Breakthourgh (hrs) 0.33* 0.5 0.5 0.5 1.0 1.0 2.0 2.0 4.0 4.0 0.5 0.5 0.33* 0.25 1.0 0.75 2.0 1.75 0.25 0.25 0.25 0.25 1.33 4.0 3.75 1 L 2.0 0.66 little or no repellent activity Example 4 Repellent Activity of CIC-3a and DEET Combinations The active ingredients, CIC-3a (2-hydroxymethylcyclohexyl propionic acid lactone), DEET, and combinations thereof in varying concentrations were applied to the shaved bellies of Rhesus monkeys. 1.2 milliliter (ml) of an ethanol solution of the compositions was applied to a 2 circle of approximately 80 cm.
Mosquitoes (female Aedas aeQvpti) were brought into contact with the treated and control areas through a cylindrical vial (approximately 375 cm 3 where both otherwise open ends were covered with a marquisette cloth through which the mosquitoes were able to bite. The cloth also ensured adequate ventilation through the vial. The open ends were approximately 80 cm 2 in area.
12- Ten to fifteen mosquitoes were placed in the vial to evaluate repellency. Prior to bringing them into contact with the treated monkey, the mosquitoes were brought into contact with an untreated area of a control monkey to sure that the mosquitoes were biting.
The results of this experiment are set forth in Table V below, wherein the total concentration of the active ingredients, concentration of CIC-3a and DEET, and the duration of observed repellency are recorded.
TABLE V Total CIC-3a DEET Breakthourgh ua (wwtl (wt% (hrs) 0.125 0.125 9 t 0999
I
09 *rr I 0.06 0.25 0.06 0.25 1.0 4.0 0.185 0.375 1.125 4.125 1.0 4.0 0.06 0.125 0.125 0.125 0.125 0 10 2.0 2.0 11 2.0 0.66 little or no repellent activity 1.33 13 Example A potentiated repellent composition is compounded in the following formula: Wt% Deet 20.0 2,3:4,5-bis(butylene) tetrahydro furaldehyde N-octyl bicycloheptene dicarboximide CIC-4 aqueous alcohol qs got$ This is a commercial type Deet formula with 2% CIC-4 added to increase the duration of effective repellency over a similar formula alone which contains no Example 6 A potentiated repellent composition is compounded in the following formula: Wt% Deet 10.0 CIC-4 2.0 2,G aqueous alcohol qs.
This is a commercial type formula employing CIC-4 to S enhance duration of repellancy while reducing the amount of Deet, thereby lowering the toxicity of the composition.
In evaluating the foregoing examples it should be borne in mind that a biological test of this kind S necessarily involves the use of numerous different animals and different batches of insects, as well as such variables as weather conditions. Therefore the data is not as numerically precise as an in vitro test, and some variations in the actual numercial readings from one series of tests to the other are inevitable but are within the skill of an experienced toxicologist to evaluate and draw valid conclusions. Such a person will focus on the 14 overall effect observed in all of the tests under all circumstances rather than attaching undue significance to an individual test result taken out of context.
We believe the foregoing data to show the decided and unexpected benefits of a composition or mixture of Deet and the subject bicyclic lactones as practical insect repellents of relatively low toxicity.
t Ct
C
I i t r t t
SC
t t tC t 15
Claims (7)
1. A potentiated insect repellent composition comprising as active repellent ingredients N, N-diethyl-meta-toluamide and a bicylic lactone compound of the formula: R' \((C22 (CH2) 0 R R'' or the corresponding unsaturated compound thereof having the formula: R' R R wherein R, R' and each are methyl or hydrogen and R'' is either methyl or hydrogen; wherein y is an integer from 1-3, and x and z each are 0 or 1, with the proviso that y is 1 or 2 when x is 1, in an amount effective to repel insects and optionally a carrier, said composition comprising a ratio of one part by weight of said bicyclic lactone to each 0.025 to 10.0 parts by weight of said toluamide wherein said potentiated insect repellent composition does not include those compositions claimed in Australian Patent 573,001.
2. The composition of claim 1 wherein R, and each are hydrogen or methyl. a 4* a a *r 0 4a 4 4, *.c 16
3. The composition of claim 1 wherein said composition comprises about 0.25-10 part by weight of said bicyclic lactone and about 0.25-20 part by weight of said toluamide.
4. The composition of claim 1, wherein said composition comprises said active ingredients in a ratio of one part by weight of said bicyclic lactone to each 0.5 to 10 parts by weight of said toluamide.
The composition of claim 1 wherein said carrier comprises an aerosol composition adapted to disperse said active ingredients into the atmosphere by means of a compressed gas.
6. The composition of claim 1 wherein said carrier is an aqueous ethanol or acetone solution.
7. A method of repelling insects from a situs comprising applying to said situs an effective amount to repel said insects of a potentiated composition comprising N, N-diethyl-meta-toluamide and a compound of the formula: R' (Cbk the formula: C (CH?) t (Co 2 Io R 17 wherein R, R' and R' each are methyl or hydrogen and R is either methyl or hydrogen; wherein y is an integer from 1-3, and x and z each are 0 or 1, with the proviso that y is 1 or 2 when x is 1; wherein said composition comprises said active ingredients in a ratio of one part by weight of said bicylic lactone to each 0.5 to 10 parts by weight of said toluamide wherein said potentiated insect repellent composition does not include those compositions claimed in Australian Patent 573,001. DATED this 22nd day of JULY, 1991 ANGUS CHEMICAL COMPANY Attorney: IAN T. ERNST Fellow Institute of Patent Attorneys of Australia of SHELSTON WATERS o o a. T- 18 o a a ;6 4
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU21424/88A AU615467B2 (en) | 1984-05-30 | 1988-08-19 | Potentiated insect repellent composition and method |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61552184A | 1984-05-30 | 1984-05-30 | |
| AU21424/88A AU615467B2 (en) | 1984-05-30 | 1988-08-19 | Potentiated insect repellent composition and method |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU42891/85A Addition AU573001B2 (en) | 1984-05-30 | 1985-05-27 | Insect repellent containing n,n-diethyl-meta-toluamide and lactone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2142488A AU2142488A (en) | 1990-06-14 |
| AU615467B2 true AU615467B2 (en) | 1991-10-03 |
Family
ID=25618284
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU21424/88A Ceased AU615467B2 (en) | 1984-05-30 | 1988-08-19 | Potentiated insect repellent composition and method |
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| Country | Link |
|---|---|
| AU (1) | AU615467B2 (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU573001B2 (en) * | 1984-05-30 | 1988-05-26 | Angus Chemical Company | Insect repellent containing n,n-diethyl-meta-toluamide and lactone |
-
1988
- 1988-08-19 AU AU21424/88A patent/AU615467B2/en not_active Ceased
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU573001B2 (en) * | 1984-05-30 | 1988-05-26 | Angus Chemical Company | Insect repellent containing n,n-diethyl-meta-toluamide and lactone |
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| Publication number | Publication date |
|---|---|
| AU2142488A (en) | 1990-06-14 |
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