Control and repellency of bed bugs

Abstract

Control or repellency of bed bugs is accomplished by bringing the bed bugs into contact with at least one of the compounds of the structure (I) ##STR00001##
Wherein
R is selected from —OH, —OC(O)R.sub.4, —OR.sub.6, —(OR.sub.6).sub.2, wherein each R.sub.6 is independently selected from an alkyl group containing from 1 to 4 carbon atoms and R.sub.4 is a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
X is O or CH.sub.2, with the proviso that when X is O, R can only be ═O;
each Z is independently selected from (CH) and (CH.sub.2)
y is a numeral selected from 1 and 2;
R.sub.1 is selected from H or a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms.
R.sub.2 is selected from H and a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms.
R.sub.3 is selected from H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, —(CH.sub.2).sub.nOH, —C(O)OR.sub.5, —CH.sub.2C(O)OR.sub.7, —CH.sub.2C(O)R.sub.8, —C(O)NR.sub.9R.sub.10, —CH.sub.2C(O)NR.sub.11R.sub.12 where each of R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 is independently selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, and n is an integer of from 1 to 12; and
the bond between the 2 and 3 positions in the ring structure may be a single or a double bond, and wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds. wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds. wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds.

Claims

1. A method for the control or repellency of bed bugs, the method comprising contacting the bed bugs with an inhibitory effective amount of at least one of the compounds (I) selected from the group consisting of: ##STR00008## ##STR00009## ##STR00010## ##STR00011##

2. The method according to claim 1 wherein the beg bugs are contacted with at least one compound (I) in combination with N,N-Diethyl-m-toluamide (DEET®).

3. The method according to claim 1 wherein the bed bugs are contacted with at least one compound (I) in combination with para-Menthane-3,8-diol (PMD).

4. The method according to claim 1 wherein the bed bugs are contacted with at least one compound (I) in combination with any other compound (I).

5. The method according to claim 1 wherein the at least one compound (I) is applied to surface of or impregnated into clothing or fabric.

6. The method according to claim 1 wherein the at least one compound (I) is applied to detergents, fabric softeners or dryer sheets.

7. The method according to claim 1 wherein the at least one compound (I) is applied as a topical repellent in lotion, wipes, powder, spray or shampoo.

8. The method according to claim 1 wherein the at least one compound (I) is selected from methyl dihydrojasmolate, ethyl dihydrojasmolate, propyl dihydrojasmolate, and prenyl dihydrojasmolate.

9. A method for the control or repellency of bed bugs, the method comprising contacting the bed bugs with an inhibitory effective amount of at least one of the compounds (I) selected from the group consisting of: ##STR00012##

10. A method for the control or repellency of bed bugs, the method comprising contacting the bed bugs with an inhibitory effective amount of at least one of the compounds (I) selected from the group consisting of: ##STR00013## ##STR00014##

Description

DETAILED DESCRIPTION OF THE INVENTION

(1) Control and repellency of bed bugs is obtained by contact of the bed bugs with an inhibitory effective amount of at least one of the compounds of the structure (I)

(2) ##STR00003##
wherein
R is selected from —OH, —OC(O)R.sub.4, —OR.sub.6, —(OR.sub.6).sub.2, wherein each R.sub.6 is independently selected from an alkyl group containing from 1 to 4 carbon atoms and R.sub.4 is a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
X is O or CH.sub.2, with the proviso that when X is O R can only be ═O;
each Z is independently selected from (CH) and (CH.sub.2);
y is a numeral selected from 1 and 2;
R.sub.1 is selected from H or a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
R.sub.2 is selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms;
R.sub.3 is selected from H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, —(CH.sub.2).sub.nOH, —C(O)OR.sub.5, —CH.sub.2C(O)OR.sub.7, —CH.sub.2C(O)R.sub.8, —C(O)NR.sub.9R.sub.10, —CH.sub.2C(O)NR.sub.11R.sub.12 where each of R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 is independently selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, and n is an integer of from 1 to 12; and the bond between the 2 and 3 positions in the ring structure may be a single or a double bond, and wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds. The invention also includes optical isomers, diastereomers and enantiomers of the named structures. Thus, at all stereocenters where stereochemistry is not explicitly defined, all possible epimers are envisioned.

(3) A preferred group of control and repellency compounds are those compounds of Structure (I) wherein

(4) R is selected from —OH, X is CH.sub.2, y is 1 or 2, each Z is selected from (CH) and (CH.sub.2), the bond between positions 2 and 3 in the ring is a single bond, one of R.sub.1 and R.sub.2 is H or —CH.sub.3 and the other of R.sub.1 and R.sub.2 is a branched or unbranched, saturated or unsaturated hydrocarbyl group containing group containing from 9 to 15 carbon atoms and 0 to 3 double bonds, and R.sub.3 is H.

(5) Another preferred group of control and repellency compounds are those compounds of structure (I) wherein

(6) R is selected from —OH, X is CH.sub.2, y is 1 or 2, more preferably 1, each Z is selected from (CH) and (CH.sub.2), the bond between positions 2 and 3 in the ring is a single or double bond, more preferably a single bond, one of R.sub.1 and R.sub.2 is H and the other of R.sub.1 and R.sub.2 is a branched or unbranched, saturated or unsaturated hydrocarbyl group containing from 9 to 15 carbon atoms and 0 to 3 double bonds, and R.sub.3 is selected from —C(O)OR.sub.5 and —CH.sub.2C(O)R.sub.8 where R.sub.5 and R.sub.8 are each selected from a branched or unbranched, saturated or unsaturated hydrocarbyl group containing from 1 to 6 carbon atoms, and more preferably 3 to 5 carbon atoms and still more preferably are —CH.sub.3.

(7) Representative examples of compounds of structure (I) include, but are not limited to,

(8) ##STR00004## ##STR00005## ##STR00006## ##STR00007##

(9) A group of especially preferred compounds of structure (I) is gamma-dodecalactone, gamma-tridecalactone, gamma-pentadecalactone, methyl apritol, methyl dihydrojasmolate, methyl dihydrojasmolate dimethyl acetal, and 3-methyl-5-pentyl-2-cyclohexenone.

(10) The inhibitory effective amount of the compounds of structure (I) to control or repel the bed bugs will be dependent upon the compound employed and the manner in which it is employed and will be readily determined by the user. In general the inhibitory effective amount will be in an amount of from about 0.1% to about 10% by weight, more preferably from about 0.1% to about 5% by weight, and more preferably from about 0.1% to about 2% by weight, in a carrier.

(11) The invention is illustrated by, but not limited to, the following examples.

(12) Two semicircle discs of paper, one treated (1 ml of acetone solution of each compound was applied to each disc) and one untreated (1 ml of acetone only), were placed in the lid of a Petri dish. Control arenas were set up in a similar fashion with two untreated discs of paper. Five replicates of 10 bed bugs were released into the centers of the lids and were thus presented with a choice of treated vs. untreated substrate (or untreated vs. untreated in the control arenas). The distribution of the bed bugs was recorded at 2 hours post-treatment. Paired t-tests were conducted for each treatment to ascertain whether or not there was a statistically significant difference in the numbers of bed bugs on the treated vs. untreated discs. Repellency, as avoidance, is given in the table below.

(13) TABLE-US-00001 TABLE 1 Compound Repellency/Avoidance DEET (0.09%) 66% DEET (0.2%) 74% Para Menthane-3,8-diol (PMD) (0.15%) 42% Para Menthane-3,8-diol (PMD) (0.2%) 70% Methyl dihydrojasmolate (0.15%) 58% Methyl dihydrojasmolate (0.2%) 82% Methyl dihydrojasmonate dimethyl acetal (0.2%) 90% Methyl dihydrojasmonate amide 28% Prenyl dihydrojasmolate (0.2%) 48% Dihydrojasmolactone (0.2%) 84% Dihydrojasmonic Acid (0.2%) 78% gamma-Dodecalactone (0.2%) 82% gamma-Tridecalactone (0.5%) 86% gamma-Tridecalactone (1%) 96% gamma-Pentadecalactone (1%) 92% gamma-Heptadecalactone (2%) 68% gamma Methyl tridecalactone (0.2%) 72% 50:50 PMD and gamma Methyl tridecalactone 98% (0.2%) Methyl apritol (0.15%) 74% Methyl apritol (0.2%) 88%

(14) While the invention has been described herein with reference to the specific embodiments thereof, it will be appreciated that changes, modifications and variations can be made without departing from the scope of the inventive concept disclosed herein, and it is intended to embrace all such changes, modification and variations that fall with the scope of the appended claims.