IL291535B2 - A repellent that mimics predator excrement - Google Patents

Description

13501-IL PREDATOR FECES MIMIC REPELLENT COMPOSITION TECHNICAL FIELD The invention relates to repellent compositions. In particular the invention relates to compositions that may be used as pest repellents or stench compositions that can be used for riot control.

BACKGROUND ART Evolution had genetically evolved prey animals to identify and avoid their predators. This includes the ability to identify the scent of a predator or its excrements such as urine or feces, used as a warning stimuli for the presence of danger. The mammalian olfactory system mediates fear responses to predator odors. Kobayakawa et al. (Nature, 2007, 450, p. 503–508) generated mutant mice in which olfactory sensory neurons in a specific area of the olfactory epithelium are ablated. The mutant mice lacked innate responses to aversive odorants, such as odors emitted from cat feces, even though they were capable of detecting them. Hence, the recognition of predator odors and innate response thereto is genetically inherent.

Animals are a costly nuisance, particularly in rural areas. Boars are responsible for $2.B per year in damage in the southern USA (USDA 2018) and in the southern hemisphere damage by rabbits is estimated by more than A$600 per year is Australia (Australian Bureau of Resource Sciences 2018). Rodents and dogs are similarly costly and often dangerous in urban areas with more than 800K attacks recorded each year in the US (CDC 2017). Animals are also an epidemiological threat. Rodents for example might transmit serious illnesses including: hantavirus, hemorrhagic fever and leptospirosis. Rock hyrax can transfer leishmaniosis.

Several attempts were made to use predator feces in order to repel pests, in particular mammals such as cats, dogs, deer and mice. See for example US Patent Application 25 13501-IL Publication Nos. 2006/263326, 2005/089543, US Patent No. 4,818,535, and Japanese Patent Application Publication Nos. 2012039984 and 2007284436. These attempts included use or mimics of processed feces or feces extracts. There are two main drawbacks in this approach. First, it requires large supply of raw manure from predators, which is difficult to obtain. Secondly, the processing obtains a product having an odor profile that diverts from the odor profile of the natural feces such that it does not necessarily stimulate an effective innate response on the pest. Thirdly, many of the materials are very volatile and are difficult to isolate in sample stored improperly Compositions bearing a strong malodor can also be used as a non-violent means to control rioting protestors. Law enforcement composition authorities around the world are seeking for effective solutions that will allow them to retain order without having casualties or injuries among the protestors. Deployment of malodor at a rioting crowd or individual is a new approach which is aimed at replacing other non-lethal weapons such as rubber bullets and tear gas. Current products suffer from ineffectiveness over the crowd and by easily removing the odor from the cloths by a simple laundry wash. There is still need for new composition that have a more deterring odor which lasts longer and is difficult to remove from the clothes and skin.

SUMMARY OF INVENTION TECHNICAL PROBLEM The aim of the invention is to provide a repelling composition that is able to mimic the natural odor profile of predator feces and induce an aversive response on prey animals, to effectively deter the pray animals from arriving or staying at a determined location or approaching an item or a subject.

SOLUTION TO PROBLEM 13501-IL In a first aspect the invention provides a repellent composition that includes a mixture of volatile compounds selected from compounds of a volatile compounds profile of predator feces.

The predator feces can be selected from feline feces such as cat feces, caracal feces, leopard feces, lion feces, tiger feces, Tigris feces, panther feces, cheetah feces or a mixture thereof. The predator feces can also be selected from canid feces such as dog feces, coyote feces, wolf feces, fox feces, boar feces, or a mixture thereof. The predator feces can be a mixture of canid and feline feces.

The volatile compounds profile may be elucidated by any suitable analytical method such as a headspace GC-MS analysis, and solid phase micro extraction (SPME) followed by GC-MS.

In some embodiments the repellant composition includes at least one linear, branched or cyclic, aliphatic or aromatic aldehyde having 2 to Error! Reference source not found. carbon atoms, at least one linear, branched or cyclic, aliphatic alcohol having 1 to 9 carbon atoms, , at least one linear or branched aliphatic carboxylic acid having 2 to 8 carbon atoms, and optionally having a sulfur atom, or linear or branched C 3 to C 8 alkyl ester thereof, at least one linear saturated or unsaturated organosulfur compound having 2 to 8 carbon atoms and one to two sulfur atoms and optionally one to two oxygen atoms, optionally at least one optionally alkyl substituted aromatic alcohol having 6 to carbon atoms and optionally at least one ketone selected from of acetone and methyl ethyl ketone.

In one embodiment, the composition of the invention mimics the volatile profile of lion feces and the composition contains: 13501-IL at least one linear, branched or cyclic, aliphatic or aromatic aldehydehaving to 9 carbon atoms, at least one linear, branched or cyclic, aliphatic alcohol having 3 to 7 carbon atoms, at least one linear or branched aliphatic carboxylic acid having 2 to 8 carbon atoms, and optionally having a sulfur atom, or linear or branched C 3 to C 8 alkyl ester thereof, at least one linear saturated or unsaturated organosulfur compound having 2 to 8 carbon atoms and one to two sulfur atoms and optionally one to two oxygen atoms, at least one lactam , optionally at least one optionally alkyl substituted aromatic alcohol having 6 to 7 carbon atoms optionally at least one ketoneselected from of acetone and methyl ethyl ketone.

In another aspect the invention provides method for preparing a repellent composition comprising the steps of: − obtaining predator feces − identifying a volatile compounds profile of predator feces, − preparing a mixture comprising identified compounds of the volatile compounds profile, − optionally adding excipients, − testing the efficacy of the composition in repelling a substrate, − in case the composition is found to be not effective, adding at least one more identified compound of the volatile compounds profile and retesting the efficacy of the composition until an effective composition is obtained, to obtain a repellent composition.

In a further aspect the invention provides a repellent composition obtainable by the above method. 25 13501-IL In another aspect the invention provides a method for repelling animals comprising applying a composition of the invention to an area from which the animals are meant to be deterred.

In yet another aspect the invention provides a riot control composition comprising a repellent composition of the invention.

In a further aspect the invention provides a riot control method comprising applying the riot control composition of the invention on at least part of the crowd.

In yet a further aspect, the invention provides an article comprising the riot control of the invention.

In another aspect the invention provides a personal protection composition comprising the repellent composition of the invention, and an article comprising the personal protection composition ADVANTAGEOUS EFFECTS OF INVENTION The invention provides a synthetic repelling composition that authentically mimics the odor profile of a predator feces, thus eliminating the need to obtain large amounts of predator manure. It has an extremely effective aversive and deterring stimuli on prey animals as well as humans.

DESCRIPTION OF EMBODIMENTS Although the invention is illustrated and described herein as embodied in example repellent compositions, the invention is not limited to the details shown because various modifications and structural changes may be made without departing from the invention and the equivalents of the claims. However, the construction and method of operation of the invention together with additional objects and advantages thereof will be best understood from the following description of specific embodiments when read in connection with the accompanying examples. 25 13501-IL The inventor of the present invention found that a composition comprising a mixture of volatile compounds that correspond to compounds that are found in the odor profile of predator feces are useful as a repellent composition. The repellent composition can be adapted for use as an animal repellent, as a non-lethal crowd control weapon or as a personal protection composition for repelling an attacker (human or animal) or a burglar.

The invention thus provides a repellent composition comprising a mixture of volatile compounds selected from compounds of a volatile compounds profile of predator feces. The volatile compounds of the mixture are selected from compounds that are detectable in a volatile compounds profile of the predator feces.

The term " repellent " refers to any composition or formulation that renders a habitat, food source, location or article unattractive to a living organism such as pests. The term " pest " is intended to include living organisms that are not wanted or cause damage to crops, gardens, food, turf, humans or other farm animals. Examples of pests include, but are not limited to, dogs, deer, raccoons, wild boars, rock hyrax and rodents such as mice and rats.

The term " volatile compounds " means in the context of this invention, compounds that evaporate from feces of a predator to the surrounding air at ambient conditions (temperature and pressure). The volatile compounds are present in the feces in an amount that allows, given their vapor pressure at ambient conditions, to be detectable by the target prey, i.e. the pest animal, and deter it. The mixture of compounds that vaporize at ambient temperatures at ambient temperatures is referred to as the " volatile compounds profile of predator feces " . Thus, the volatile compounds profile is the mixture of compounds that are obtainable by collection of the volatile materials emitted from predator feces. In one embodiment, the volatile compounds profile is elucidated from a common analytical method for determining the presence of volatile compounds such as headspace GC-MS analysis or collection of the volatile materials by solid phase microextraction (SPME) in a headspace above a vial or container that 13501-IL contains predator feces followed by release into a GC-MS device. In some embodiments, said analysis is performed by running a chromatographic analysis of feces obtained from a predator. GCMS has the ability to see very low concentrations. With the most abundant material defined as 100%, materials were identified to a relative concentration of 0.01%. Materials below this were deemed too dilute to matter.

In some embodiments the composition comprises the list of volatile compounds that are elucidated from the analytical analysis as described above having the weight ratio between the various compounds being equivalent to the relative signal integral. This is a close approximation to the actual weight ratio of the compounds, as the signal integral is closely proportional to the spectral absorbance of each compound. In some embodiments a correction factor taking deviations from linear proportionality of each compound signal is taken into account.

As different compounds in the volatile compounds profile have different vapor pressure at a given temperature and pressure, a mixture comprising the volatile compounds profile in weight ration equivalent to their spectral weight ration may provide a volatile profile of its own which diverts from the ration of the volatile profile of the feces. Thus, according to some embodiments the weight ratio of each compound in the composition is normalized such that its weight ratio is inversely proportional to its vapor pressure.

In some embodiments the composition comprises only the major components in the volatile compounds profile. In some embodiments, the composition comprises the top 5, 7, 10, 15, 20 or 25 compounds appearing in the volatile compounds profile.

In some embodiments the composition comprises only those compounds of the volatile compounds profile having a LD 50 rat value lower than 200, 500 or 1000 mg/KG body weight or equivalent (i.e. when the literature value is measured in mL/Kg body weight). 13501-IL In order to achieve a composition that mimics the odor of the predator feces, in some embodiments the composition comprises at least 60%, 70%, 75%, 80%, 85%, 90% of the compounds of the volatile compounds profile as defined above. The composition of the invention may comprise at least 75% of the compounds that are present in the volatile compounds profile of the predator feces.

The term predator relates to an animal that preys its food, i.e. a carnivore. In some embodiments the predator feces is selected from feline feces or canid feces. The term " feline feces " refers to feces of a cat or a member of the cat family (Felidae). The family includes inter alia domestic cat, caracal, leopard, lion, tiger, Tigris, panther and cheetah. The term " canid feces " refers to feces of a member of the canidea family that include domestic dogs, wolves, coyotes, foxes, jackals, bears and other types of dog-like mammals.

In some embodiments the predator feces mimic compositions of the invention are prepared as a concentrate and diluted to application strength or admixed with an appropriate particulate matter when used. The predator feces mimic compositions may be diluted with water. The water may be ionized, distilled, filtered, spring, purified, mineral or sterile. In some embodiments the composition can be diluted in water in a 1:100 to 100:1 v/v ratio. In some embodiments the composition can be diluted in water in a 10:90 to 90:10 v/v ratio. In some embodiments the composition can be diluted in water in a composition/water 30:70 to 70:30 v/v ratio. In some embodiments the composition can be diluted in water in a composition/water 70:30 to 80:20 v/v ratio. In some embodiments the composition can be diluted in water as a composition/water 75:25 v/v ratio. In some embodiments the composition of the invention can be formulated as an aqueous solution, oil in water emulsion, water in oil emulsion or aqueous suspension wherein the volume of the composition out of the total volume of the formulation is between 1-90 % V/V In some embodiments, the composition further comprises at least one additional active agent that is known in the art to act as an animal repellent. For example, the 13501-IL composition may include ortho-aminoacetophenone, methyl nonyl ketone, castor oil, geraniol oil, rosemary oil, citronella oil predator glandular secretions and predator urine. In some embodiments, irritants (i.e. compounds that cause an irritating effect to animals or humans) such as formic acid or capsaicin are added to the mixture.

The compositions of this invention may be formulated as an aerosol, emulsion, solution, cream, lotion or gel. In some embodiments, the composition of the invention can be formulated as an oil in water emulsion, water in oil emulsion or aqueous suspension.

When the compositions of the invention are formulated into an aqueous emulsion, emulsifiers may be added to better emulsify or disperse the ingredients of the composition. Without being limited thereto, emulsifiers that can be selected from sorbitan oleate materials (SPAN) and their polyethylene glycol derivatives (TWEEN), sodium alkylaryl sulfonates, alkyl thios, alkylarylpolyether alcohols, sodium polyglycol ether sulfonates, purified sodium lignosulfonate, sodium lauryl alcohol sulfate, and mixtures thereof.

The compositions of this invention can be formulated for use in pressurized aerosol dispensing containers. In such embodiments the composition of the invention is admixed with a suitable propellant as known in the art.

One of the objectives of the present invention is to enhancing the deposition of fragrance on target substrates and to prolong the duration of release of the fragrance molecules in the composition is highly desirable. Controlling the release of the different fragrance compounds with respect to time. Some fragrance compounds, especially those which are highly volatile can be quickly lost due to evaporation and they tend to dissolve easily in aqueous media and be rinsed away. This challenge can be addressed by "extenders" or "slow release agents" which are usually polymer particles, that selectively adsorb/absorb or dissolve highly volatile or semi-volatile fragrance compounds and enhance deposition from rinse-off by water, affecting slow release of 13501-IL the fragrance compounds when the composition is exposed to air, thereby prolonging the effectiveness of the fragrance compounds.

Extenders as described above are known in the art. Any extender known in the art can be used in order to formulate the compositions of the invention as extend release formulations. In some embodiments, the extenders are polymeric particles. In some embodiments microporous resins can be used. In some embodiments the polymeric particle is a selective perfume-releasing polymer. In some embodiments the polymeric particle is a copolymer of ethylene and a polar vinyl monomer such as polyethylvinyl acetate. In some embodiments the polymeric particle is selected from the group consisting of polymethylamino alkyl acrylates, polyvinyl pyrrolidones, polyvinyl imidazoyls, polyvinyl ethers with diethylamino groups, polyvinylpyridines, alkylated polyacrylamides, polyalkylaminoalkyl acrylamide, and copolymer of polymethyl methacrylate and polymethyl aminoethyl methacrylate cross-linked with polyethylene glycol dimethacrylate.

When adding extenders to the composition, the person of skill in the art would know to choose the amount of extender in order to ensure that the volatile compounds are released from the extender in an effective amount to repel the animal. The concentration of repellent composition in the extender may range from 10% to 90% by weight, in some embodiments between 20% and 80%, and in some embodiments between about 30% and 70%.

The composition may be formulated with excipients as known in the art. The excipients are selected from a group consisting of carriers, surface active agents, thickeners, binders, fillers, diluents, colorants, preservatives, sorbents, extenders and combinations thereof.

Carriers may be selected from the group consisting of bentonite, fullers earth, additional clays, talc, chalk, quartz, montmorillonite or diatomaceous earth, vermiculite, highly dispersed silicic acid, alumina and silicates, calcite, marble, pumice, 13501-IL sepiolite and dolomite, inorganic and organic meals, sawdust, coconut shells, corn cobs and tobacco stalks.

Surface-active agents useful in the present compositions may be selected from the group consisting of polyethylene oxide esters of fatty acids, polyethylene oxide ethers of fatty alcohols, alkyl sulfates, alkyl sulfonates, aryl sulfonates, albumin hydrolyzates, and especially alkyl arylpolyglycol ethers, magnesium stearate, sodium oleate, lignin, lecithin, sulfite waste liquors and methyl cellulose.

Thickeners useful in the present invention may be selected from the group consisting of agar, corn starch, potato starch and guar gum.

The repellent compositions of the present invention may be applied via painting, brushing, mopping, spreading, banding, broadcasting, side-dressing, coating, rolling, bathing, dipping, immersing, soaking, adhering, sticking, rubbing, wiping, impregnating, injecting, embedding, sealing, stippling, dotting, dabbing, stenciling, stamping, layering, spackling, sprinkling, spraying, misting, dusting, jet spraying, aerial application, vaporizing, pouring and combinations thereof. The term aerial application includes, but is not limited to, distribution from an aircraft.

The repellent composition can be adapted in some embodiments for use as an animal repellant and in some embodiments for use as a non-lethal crowd control weapon.

When adapted for use as an animal repellent, the repellent composition may further include masking agents, that will improve its’ sent for humans while maintaining its potency as a repellent for animals. In order to increase its effectiveness against a particular animal, other compounds that are known in the art to repel the particular animal may be added to the composition.

In some embodiments, the composition mimics the volatile profile of feline feces (" feline feces mimic composition "). The feline feces mimic composition may include at least one aldehyde, at least one aliphatic alcohol, at least one carboxylic acid, at least 13501-IL one organosulfur compound optionally at least one amine, optionally at least one aromatic alcohol, optionally at least one heteroaromatic bicyclic compound and optionally at least one ketone.

The feline feces mimic composition may comprise at least one linear, branched or cyclic, aliphatic or aromatic aldehyde having 2 to 9 carbon atoms, at least one linear, branched or cyclic, aliphatic alcohol having 1 to 7 carbon atoms, at least one linear or branched aliphatic carboxylic acid having 2 to 8 carbon atoms, and optionally having a sulfur atom, or linear or branched C 3 to C 8 alkyl ester thereof, at least one linear saturated or unsaturated organosulfur compound having 2 to 8 carbon atoms and one to two sulfur atoms and optionally one to two oxygen atoms, optionally at least one optionally alkyl substituted aromatic alcohol having 6 to 7 carbon atoms, and optionally at least one Ketone selected from of acetone and methyl ethyl ketone.

In some embodiments the composition is characterized by including – 0.1 – 35 % w/w, 1 -30 % w/w, 1 - 25 % w/w or 2 – 12 % w/w out of the total weight of the composition of at least one linear, branched or cyclic, aliphatic or aromatic aldehyde having 2 to 9 carbon atoms, 0 – 20 % w/w, 0.1 – 20 % w/w, 1 – 15 % w/w or 1 – 5 % w/w out of the total weight of the composition of at least one linear, branched or cyclic, aliphatic alcohol having to 9 carbon atoms, 0.1 – 30 % w/w, 1 - 25 % w/w, 2 - 25 % w/w or 3 – 12 % w/w out of the total weight of the composition of at least one optionally alkyl substituted aromatic alcohol having to 7 carbon atoms, – 85 % w/w, 10 – 80 % w/w or 15 – 75 % w/w out of the total weight of the composition of at least one linear or branched aliphatic carboxylic acid and optionally having a sulfur atom, or linear or branched C 3 to C 6 alkyl ester thereof, 25 13501-IL 0.05 – 15 % w/w, 0.1 – 15 % w/w or 0.15 – 11 % w/w out of the total weight of the composition of at least one linear organosulfur compound having 2 to 8 carbon atoms and one to two sulfur atoms, 0.05 – 10 % w/w, 0.1 – 5 % w/w or 0.1 – 1 % w/w out of the total weight of the composition of at least one heteroaromatic compound having 8 carbon atoms and one nitrogen atom, 0.01 – 15 % w/w, 0.05 – 10 % w/w or 0.05 – 1 % w/w out of the total weight of the composition of at least one lactam and - 0 – 85 % w/w, 0 – 75 % w/w, 0 – 65 % w/w of at least one of acetone and methylethylketone (MEK). The latter two ketones are usually found in the vapor profile of predator feces, and in particular feline feces especially lion feces. However, as these compounds are extremely volatile, they might not last long after the composition is applied to the subject area or article, thus, in some embodiments they may be present in small amounts (i.e., in the lower end of the aforementioned range, for example 10- % w/w) or even omitted all together from the composition.

In some embodiments the repellent composition mimics the volatile profile of lion feces (" lion feces mimic composition "). In such an embodiment the composition may include at least one aldehyde, at least one aliphatic alcohol, at least one aromatic alcohol, at least one carboxylic acid, at least one organosulfur compound and at least one heteroaromatic bicyclic compound and optionally at least one ketone.

In some cases, compounds with little to no scent or very high volatility were not added to the mixture. In some cases, compounds that are not commercially available or costly materials were not added to the mixture. In some cases, compounds having a toxicity of level of LD 50 oral rat value lower than 100, 250, 500 or 1000 mg/KG body weight or equivalent (i.e. when the literature value is measured in mL/Kg body weight) were excluded from the mixture. 13501-IL The at least one aldehyde in the lion feces mimic composition is a linear, branched or cyclic, aliphatic or aromatic aldehyde having 2 to 14, in some embodiments 2 to 11 or to 9 carbon atoms, optionally selected from acetaldehyde, isovaleraldehyde, pivaldehyde, benzaldehyde, octanal and nonal.

The at least one aliphatic alcohol in the lion feces mimic composition is at least one linear, branched or cyclic, aliphatic alcohol having 4 to 10, 4 to 9, 4 to 8, 5 to 8 and in some embodiments 5 to 7 carbon atoms, optionally selected from iso-pentyl alcohol, and pentanol.

The at least one aromatic alcohol in the lion feces mimic composition is an optionally alkyl substituted aromatic alcohol having 6 to 12, in some embodiments 6 to 10, in some embodiments 6 to 9, in some embodiments 6 to 8 and in some embodiments to 7 carbon atoms, optionally selected from cresol and phenol.

The at least one carboxylic acid in the lion feces mimic composition has 2 to 12, 2 to 10, to 9, 2 to 8, 2 to 7 or 2 to 6 carbon atoms and optionally having a sulfur atom optionally selected from acetic acid, butyric acid, 4-methyl valeric acid, and valeric acid, or linear or branched C 1 to C 8, C 2 to C 7 or C 3 to C 6 alkyl esters thereof optionally selected from propyl, iso-propyl and hexyl esters.

The at least one organosulfur in the lion feces mimic composition has 2 to 12, 2 to or 2 to 8 carbon atoms and one to four or one to two sulfur atoms and optionally one to four or one to two oxygen atoms, the at least one organosulfur is selected independently from the optional carboxylic acid comprising a sulfur atom, i.e. in case the composition comprises a carboxylic acid having a sulfur atom the composition additionally comprises another organosulfur compound.

The at least one lactam is optionally 2-piperidone.

The at least one heteroaromatic bicyclic compound has 6 to 10, 7 to 9 or 8 carbon atoms and one to two or one nitrogen atom. 13501-IL The optionally one ketone is selected from acetone and methyl ethyl ketone.

In some embodiments the lion feces mimic composition further comprises at least one of triethylamine, δ-valerolactam and 2,5-dimethylpiperazine.

In some embodiments amines that are present in the lion feces mimic composition form ammonium salts with the carboxylic acids also present in the composition. This may contribute to a slow release of said components from the composition.

In some embodiments the lion feces mimic composition comprises: 0.1 – 35 % w/w, 1 -30 % w/w, 1 - 25 % w/w or 2 – 12 % w/w out of the total weight of the composition of at least one linear, branched or cyclic, aliphatic or aromatic aldehyde having 2 to 9 carbon atoms, 0 – 20 % w/w, 0.1 – 20 % w/w, 1 – 15 % w/w or 1 – 5 % w/w out of the total weight of the composition of at least one linear, branched or cyclic, aliphatic alcohol having to 7 carbon atoms, 0.1 – 30 % w/w, 1 - 25 % w/w, 2 - 25 % w/w or 3 – 12 % w/w out of the total weight of the composition of at least one optionally alkyl substituted aromatic alcohol having 6 to 7 carbon atoms, – 85 % w/w, 10 – 80 % w/w or 15 – 75 % w/w out of the total weight of the composition of at least one linear or branched aliphatic carboxylic acid and optionally having a sulfur atom, or linear or branched C 3 to C 6 alkyl ester thereof, 0.05 – 15 % w/w, 0.1 – 15 % w/w or 0.15 – 11 % w/w out of the total weight of the composition of at least one linear organosulfur compound having 2 to 8 carbon atoms and one to two sulfur atoms, 13501-IL 0.05 – 10 % w/w, 0.1 – 5 % w/w or 0.1 – 1 % w/w out of the total weight of the composition of at least one heteroaromatic compound having 8 carbon atoms and one nitrogen atom, 0.01 – 15 % w/w, 0.05 – 10 % w/w or 0.05 – 1 % w/w out of the total weight of the composition of at least one lactam and - 0 – 85 % w/w, 0 – 75 % w/w, 0 – 65 % w/w of at least one of acetone and methylethylketone (MEK). The latter two ketones are usually found in the vapor profile of predator feces, and in particular feline feces especially lion feces. However, as these compounds are extremely volatile, they might not last long after the composition is applied to the subject area or article, thus, in some embodiments they may be present in small amounts (i.e., in the lower end of the aforementioned range, for example 10- % w/w) or even omitted all together from the composition.

In some embodiments the lion feces mimic composition comprises 7 – 9 % w/w isovaleraldehyde, 4 – 6 % w/w acetic acid, 0 – 2 % w/w isopentyl alcohol, 0.5 – 1.5 % w/w methyl disulfide, 3 – 4 % w/w propionic acid, 0 – 3 % w/w pentanol, 5 – 10 % w/w isobutyric acid, 10 – 15 % w/w butyric acid, 9 – 14 % w/w isovaleric acid, 6 – 9 % w/w 2-methylbutyric acid, 10 – 15 % w/w valeric acid, 0.1 – 0.5 % w/w isopropyl valerate, – 0.1 % w/w propyl 2-methylbutanoate, 0 – 0.1 % w/w propyl valerate, 0.2 – 0.3 % w/w isobutylacetic acid, 0.5 – 1.0 % w/w benzaldehyde, 4.5 – 5 % w/w phenol, 0.2 – 0.3 % w/w hexyl pentanoate, 0.1 % w/w octanal, 6 – 7 % w/w cresol, 0.1 – 0.3 % w/w nonanal, 0.2 – 8 % w/w 2-piperidone, and 0.3 - 0.5 % w/w indole out of the total weight of the composition.

In some embodiments the lion feces mimic composition comprises 0 – 70 % w/w acetone, 0 – 10 % w/w MEK, 2 – 9 % w/w isovaleraldehyde, 0.5 – 6 % w/w acetic acid, – 2 % w/w isopentyl alcohol, 0.1 – 1.5 % w/w methyl disulfide, 0.5 – 4 % w/w propionic acid, 0 – 3 % w/w pentanol, 1 – 10 % w/w isobutyric acid, 1 – 15 % w/w butyric acid, – 14 % w/w isovaleric acid, 1 – 9 % w/w 2-methylbutyric acid, 1 – 15 % w/w valeric acid, 13501-IL 0.1 – 0.5 % w/w isopropyl valerate, 0 – 0.1 % w/w propyl 2-methylbutanoate, 0 – 0.1 % w/w propyl valerate, 0.01 – 0.3 % w/w isobutylacetic acid, 0.05 – 1.0 % w/w benzaldehyde, 0.1 – 5 % w/w phenol, 0.02 – 0.3 % w/w hexyl pentanoate, 0.1 % w/w octanal, 0.5 – 7 % w/w cresol, 0.01 – 0.15 % w/w nonanal, 0.02 – 8 % w/w 2-piperidone, and 0.05 – 0.2 % w/w indole out of the total weight of the composition.

Any compound mentioned above may be present in amounts between or bounded by those recited herein.

The lion feces composition can be useful as an animal repellent in repelling a wide range of pest animals. This may include for example dogs, deer, wild boars, rock hyrax, rabbits and rodents such as mice and rats.

The lion feces composition is also extremely stringent for humans that remains potent after days when applied to clothing. As such, the composition can be formulated into a non-lethal riot control weapon. Currently used compositions for this sake have been found to be poorly effective, thus the present composition has promising prospects in providing a long needed alternative.

In another embodiment, the invention provides a cat feces mimic composition. The cat feces mimic composition comprises, according to the general concept of the invention, a mixture of volatile compounds that are detectable in an analytical profiling of the vapors that are emitted from cat feces as analyzed by an analytical method such as a headspace GC-MS analysis.

In some cases, compounds with little to no scent or very high volatility were not added to the mixture. In some cases, compounds that are not commercially available or costly materials were not added to the mixture. In some cases, compounds having a toxicity of level of LD 50 oral rat value lower than 100, 250, 500 or 1000 mg/KG body weight or equivalent (i.e. when the literature value is measured in mL/Kg body weight) were excluded from the mixture. 13501-IL A cat feces mimic composition according to the invention may include at least one aldehyde, at least one aliphatic alcohol, at least one aromatic alcohol, at least one carboxylic acid, at least one organosulfur compound, at least one amine compound and at least one heteroaromatic bicyclic compound.

The cat feces mimic composition has been found to be extremely useful as an animal repellent against rodents, in particular mice. When brought in contact with mice, the mice either deterred from the area to which the composition is applied, and in a confined area (e.g. a bathtub) the mice became motionless for hours, pretending to be dead.

According to an embodiment of invention, the cat feces comprises: at least one linear, branched or cyclic, aliphatic or aromatic aldehyde having 2 to carbon atoms, at least one linear, branched or cyclic, aliphatic alcohol having 1 to 7 carbon atoms, at least one optionally alkyl substituted aromatic alcohol having 6 to 7 carbon atoms, at least one linear or branched aliphatic carboxylic acid having 2 to 6 carbon atoms and optionally having a sulfur atom, at least one linear saturated or unsaturated organosulfur compound having 2 to carbon atoms and one to two sulfur atoms and optionally one to two oxygen atoms, at least one lactam, and and optionally a ketone selected from acetone and methyl ethyl ketone or mixture thereof.

In some embodiments the cat feces mimic composition comprises: 13501-IL 1 – 65 % w/w, 5 - 55 % w/w, 15 - 45 % w/w or 25 – 40 % w/w out of the total weight of the composition of at least one linear, branched or cyclic, aliphatic or aromatic aldehyde having 2 to 9 carbon atoms, 1 – 35 % w/w, 1 – 30 % w/w, 5 – 25 % w/w or 10 – 20 % w/w out of the total weight of the composition of at least one linear, branched or cyclic, aliphatic alcohol having 5 to 7 carbon atoms, 0.1 – 20 % w/w, 0.5 - 15 % w/w, 1 - 10 % w/w or 3 – 5 % w/w out of the total weight of the composition of at least one optionally alkyl substituted aromatic alcohol having to 7 carbon atoms, – 50 % w/w, 10 – 40 % w/w or 15 – 30 % w/w out of the total weight of the composition of at least one linear or branched aliphatic carboxylic acid and optionally having a sulfur atom 1 – 30 % w/w, 5 – 25 % w/w or 10 – 20 % w/w out of the total weight of the composition of at least one linear organosulfur compound having 2 to 8 carbon atoms and one to two sulfur atoms, 0 – 2 % w/w, 0.1 – 1 % w/w or 0.3 – 0.5 % w/w out of the total weight of the composition of at least one amide having 1 to 3 carbon atoms and - 0 – 50 % w/w, 0 – 40 % w/w, 0 – 30 % w/w of at least one of acetone and methylethylketone (MEK).

In some embodiments the cat feces mimic composition comprises acetaldehyde, methanol, formamide, acetic acid, isopropyl alcohol, isopentyl alcohol, isobutyric acid, 3-methyl-buten-1-thiol, butyric acid pivaldehyde, 3-methyl-buten-1-ol, 2-methylbutyric acid, acetamide, valeric acid, octane thiol, isobutylacetic acid, benzaldehyde, dimethyl sulfone, octanal, cresol, and thioglycolic acid. 13501-IL In some embodiments the cat feces mimic composition comprises 0 – 25 % w/w acetone, 0 – 5 % w/w MEK, 15 – 25 % w/w acetaldehyde, 0.5 – 6 % w/w acetic acid, 1 -% w/w methanol, 0.05 – 1 % formamide, 10 - 20 % w/w acetic acid, 1 – 7 % w/w isopropyl alcohol, 1 – 8 % w/w isopentyl alcohol, 2 – 8 % w/w 3-methyl- 2-butene-1-thiol, 0.1 – 1 % w/w butyric acid, 1 – 5 % w/w pivaldehyde, 0.1 – 1 % w/w 3-methyl- 2- butene-1-thiol, 0.1 – 3 % w/w 2-methylbutyric acid, 0.05 – 1 % w/w acetamide, 0.5 –% w/w valeric acid, 1 – 10 % w/w octane thiol, 1 – 5 % w/w isobutylacetic acid, 1 – 7 % w/w benzaldehyde, 1- 5 % w/w dimethyl sulfone, 0.5 – 7 % w/w octanal and 0.5 – 7 % w/w cresol, out of the total weight of the composition.

Any compound mentioned above may be present in amounts between or bounded by those recited herein.

In some embodiments the repellent composition mimics the volatile profile of tiger feces (" tiger feces mimic composition "). In such an embodiment the composition may include at least one aldehyde, at least one aliphatic alcohol, optionally at least one aromatic alcohol, at least one carboxylic acid, at least one organosulfur compound, at least one α,β-hydroxyacid optionally at least one C 18 – C 36 aliphatic hydrocarbon and optionally at least one ketone.

In some cases, compounds with little to no scent or very high volatility were not added to the mixture. In some cases, compounds that are not commercially available or costly materials were not added to the mixture. In some cases, compounds having a toxicity of level of LD 50 oral rat value lower than 100, 250, 500 or 1000 mg/KG body weight or equivalent (i.e. when the literature value is measured in mL/Kg body weight) were excluded from the mixture.

The at least one aldehyde in the tiger feces mimic composition is a linear, branched or cyclic, aliphatic or aromatic aldehyde having 2 to 14, in some embodiments 2 to 11 or 2 to 9 carbon atoms, optionally selected from acetaldehyde, isovaleraldehyde, pivaldehyde, benzaldehyde, octanal and nonal. 13501-IL The at least one aliphatic alcohol in the tiger feces mimic composition is at least one linear, branched or cyclic, aliphatic alcohol having 4 to 10, 4 to 9, 4 to 8, 5 to 8 or 5 to carbon atoms, optionally selected from iso-pentyl alcohol, pentanol and octanol.

The optionally at least one aromatic alcohol in the tiger feces mimic composition is an optionally alkyl substituted aromatic alcohol having 6 to 12, in some embodiments 6 to 10, in some embodiments 6 to 9, in some embodiments 6 to 8 and in some embodiments 6 to 7 carbon atoms, optionally selected from 2,3-dihydroxybenzoic acid.

The at least one carboxylic acid in the tiger feces mimic composition has 2 to 12, 2 to 10, 2 to 9, 2 to 8, 2 to 7 or 2 to 6 carbon atoms and optionally having a sulfur atom optionally selected from acetic acid, butyric acid, iso-butyric acid, 4-methyl valeric acid, iso-valeric acid and valeric acid, or linear or branched C 1 to C 8, C 2 to C 7 or C 3 to C 6 alkyl esters thereof optionally selected from propyl, iso-propyl and hexyl esters.

The at least one optionally organosulfur in the tiger feces mimic composition has 2 to 12, 2 to 10 or 2 to 8 carbon atoms and one to four or one to two sulfur atoms and optionally one to four or one to two oxygen atoms, the at least one organosulfur is selected independently from the optional carboxylic acid comprising a sulfur atom, i.e. in case the composition comprises a carboxylic acid having a sulfur atom the composition additionally comprises another organosulfur compound. The organosulfur compound may be dodecane thiol.

The optionally one ketone is selected from acetone and methyl ethyl ketone.

In some embodiments the tiger feces mimic composition further comprises at least one of triethylamine, δ-valerolactam and 2,5-dimethylpiperazine.

In some embodiments amines that are present in the tiger feces mimic composition form ammonium salts with the carboxylic acids also present in the composition. This may contribute to a slow release of said components from the composition. 25 13501-IL In some embodiments the tiger feces mimic composition comprises: 0.1 – 35 % w/w, 1 -30 % w/w, 1 - 25 % w/w, 1 – 12 % w/w or 1-3 % w/w out of the total weight of the composition of at least one linear, branched or cyclic, aliphatic or aromatic aldehyde having 2 to 9, 3 to 7 or 4 to 6 carbon atoms, 0 – 20 % w/w, 0.1 – 20 % w/w, 1 – 15 % w/w or 7 – 12 % w/w out of the total weight of the composition of at least one linear, branched or cyclic, aliphatic alcohol having to 9, or 5 to 8 carbon atoms, – 85 % w/w, 10 – 80 % w/w or 15 – 75 % w/w out of the total weight of the composition of at least one linear or branched aliphatic carboxylic acid and optionally having a sulfur atom, or linear or branched C 3 to C 6 alkyl ester thereof, 0.05 – 15 % w/w, 0.1 – 15 % w/w, 1 – 10 % w/w or 4 – 6 % w/w out of the total weight of the composition of at least one linear organosulfur compound having 2 to 8 carbon atoms and one to two sulfur atoms, and optionally 0 – 85 % w/w, 0 – 75 % w/w, 0 – 65 % w/w or 1 – 20 % w/w of at least one of acetone and methylethylketone (MEK). The latter two ketones are usually found in the vapor profile of predator feces, and in particular feline feces especially tiger feces. However, as these compounds are extremely volatile, they might not last long after the composition is applied to the subject area or article, thus, in some embodiments they may be present in small amounts (i.e., in the lower end of the aforementioned range, for example 10- 20 % w/w) or even omitted all together from the composition.

The tiger feces mimic composition may comprise 1- 20 % w/w acetone, 1 – 5 % w/w butanone, 1 – 2 % w/w octanal, 1 – 2 % w/w nonal, 1 – 2 % w/w isobutyric acid, 0.01 – 0.5 % w/w 4-methylvaleric acid, 1 – 2 % w/w 3- methyl butyraldehyde isovaleraldehyde, – 3 % w/w isovaleric acid, 1 – 3 % w/w valeric acid, 0.01 – 0.5 % w/w isopropyl valerate, 0.01 – 0.5 % w/w butyric acid, 1 – 3 % w/w 4-hydroxypentanone, 0.01 – 0.5 % 25 13501-IL w/w pentanol, 1 to 5 % w/w C 8 to C 12 aliphatic thiols, and 3 – 6% isoamyl alcohol out of the total weight of the composition.

Any compound mentioned above may be present in amounts between or bounded by those recited herein.

The tiger feces composition can be useful as an animal repellent in repelling a wide range of pest animals. This may include for example dogs, deer, wild boars, rock hyrax, rabbits and rodents such as mice and rats.

The tiger feces composition is also extremely stringent for humans that remains potent after days when applied to clothing. As such, the composition can be formulated into a non-lethal riot control weapon. Currently used compositions for this sake have been found to be poorly effective, thus the present composition has promising prospects in providing a long needed alternative.

In another aspect, the invention provides a method for preparing a repellent composition. Reference is made to Figure 1 depicting an exemplary embodiment (1000) of the method. First (100), predator feces are obtained. The predator feces can be obtained for example from a zoo or a big cats sanctuary, or an animals SOS shelter in the case of dogs or cats. In some embodiment, fresh feces are used to determine the volatile profile of the feces. Feces that are up to 24 hours old are considered in this context as being " fresh feces ", afterwards the material can be stored longer in a closed, airtight container and frozen. Feces that are also exposed to urine are not acceptable. Fresh feces also contain a certain level of water content. In some embodiments the feces contain up to 50% w/w water. Feces can be mixed with other materials such as hair and other excretions.

The volatile compounds profile of the predator feces is then analyzed and characterized (102) and the different compounds that are emitted from the feces are identified and a characterization of the volatile profile of the feces is obtained. The identification of the volatile profile can be carried out by any commonly used method that is applied in 13501-IL the art in order to determine chemical components of a mixture, in particular a volatile mixture. For example, as mentioned above, this may include static or dynamic head space gas chromatography mass spectroscopy (GC/MS). GC flame ionization (GC-FID) or GC electron capture (GC-ECD) can also be used. In some embodiments SPME GC/MS is applied. In some embodiments the profile is determined by Purge-and-trap concentrator, thermal desorption to air page.

Identification of the volatile chemical can be determined by mass spectroscopy. The molecular weight provides an initial identification. This is further confirmed by comparison to the NIST library (standard in all modern GCMS). Other libraries may also be used.

After the volatile compounds profile of the predator feces has been determined, compounds from the list of compounds that were identified are mixed together (104) to obtain a mixture of volatile compounds that mimics the volatile compounds profile of the predator feces.

The relative quantities of the compounds in the mixture can be equivalent to the relative intensities of their spectral signals in the spectral analysis that determined the volatile compounds profile. In some embodiments it may deviate for the relative ratios of the spectral signals by 10-50%. In some embodiments the relative quantities are normalized by the vapor pressure of each compound.

In some embodiments all the compounds that were identified are added to the mixture. In some embodiments only the top 5, 10, 15 or 20 compounds (in terms of quantity, i.e. signal intensity) are added to the mixture. In some embodiments any compound having a concentration greater than 0.01% relative concentration is added to the mixture. In some cases, compounds with little to no scent or very high volatility were not added to the mixture. In some cases, compounds that are not commercially available or costly materials were not added to the mixture. 13501-IL The preparation may also include a step of identifying the compounds being non-toxic out of the volatile compounds profile and mixing only these identified compounds out of the volatile compounds profile to form the composition. The non-toxic compounds may be defined as compounds having a LD 50 oral rat value lower than 100, 250, 500 or 1000 mg/KG body weight or equivalent (i.e. when the literature value is measured in mL/Kg body weight).

The compounds can be obtained from any chemicals provider resource or prepared by conventional synthetic procedures.

Excipients as detailed above can be added to the mixture in order to formulate it into an applicable product (105).

The predator feces mimic composition that is obtained is then tested for its efficacy in repelling a substrate (106). This may be done, for example, by applying the composition to a cloth and bringing the cloth close to an animal being the subject for repelling or by applying the material to an area from which the animal is supposed to be deterred. A solution comprising only the excipients and/or solvents without the mixture of volatile compounds, can be used as control. The efficacy of the composition is determined according to observation of the behavior of the pest animals. This may include the response time to deterring the animal, the duration after applying the composition that the animals are deterred from the area at different weather conditions and time of day, the radius of efficacy, and the effect on the aggressiveness of the animal or other behavioral patterns and so forth.

In case the composition is found to be not effective (108), or not satisfactory, at least one more identified compound of the volatile compounds profile can be added to the mixture (110) to obtain a modified mixture. The modified mixture is retested for efficacy (108) and in case it is still not effective steps 110 and 108 are reiterated, until an effective composition is obtained. On the other hand, if the composition is found to be effective, a new composition can be prepared without at least one of the identified 13501-IL compositions (112), in order to determine whether the identified compound that was left out of the mixture of volatile compounds is essential for obtaining an effective composition. In case the composition is found to be non-effective, then the last compound that was removed from the mixture is reintroduced (116) to obtain an effective mixture (or composition). Steps 112 and 114 can be reiterated with any of the ingredients until a minimal number of essential ingredients achieving efficacy is obtained.

According to another aspect, the invention provides any repellent composition that can be obtained according to the method described above.

The repellent compositions of the invention are applied in desired indoor or outdoor locations, boundaries or articles such as on floor panels, grass lawns, fences, food storage items such as pantries and refrigerators, around the base of a tree, a tent, personal accessories, apparel, a backpack, interior or exterior parts of a vehicle, in particular a recreational vehicle, an edge of a door, or on top of or under a piece of furniture. The devices can also be directly attached to an object or area to be protected. The repellent composition can also be formulated to be compatible for applying it on cloths or directly on the skin. To this end, the repellent composition is formulated as an aerosol, crème, gel or lotion. The person versed in the art would know how to formulate the composition for this purpose according to commonly used methods in the art.

The invention further provides a riot control composition, which comprises any of the repellent compositions of the invention. According to an embodiment of the invention the riot control composition comprises the lion feces mimic composition of the invention.

When the composition is formulated for use as non-lethal riot control composition, the composition may further include an additional malodorous active ingredient known in the art. A malodorous compound is defined herein as a compound having an extreme 13501-IL stench that when coming in contact with a human subject may induce discomfort, nausea and/or vomiting. Non-limiting examples of malodorous compounds include organosulfur compounds.

The non-lethal crowd control composition can be packaged in various types of containers in order to make it applicable for use as a weapon. For example, the non- lethal crowd control composition can be placed in a water tank of a water cannon vehicle. It can also be placed in a canister that adds a small volume of a concentrate of the non-lethal crowd control composition to a jet of water when the jet of water is shot at the crowd from a water cannon vehicle. The non-lethal crowd control composition can also be packaged in a projectile of a gun, a hand held canister and a malodor grenade.

Therefore, an article comprising the crowd control composition of the invention is in the scope of the current invention, wherein the article can be a malodor grenade, a projectile of a gun, a water cannon malodor cylinder and a water cannon reservoir tank In some embodiments an odor intensifier is added to the composition for the purpose of intensifying the odor of the composition. Any odor intensifier that is commonly used in the perfume industry can be used in the context of the present invention. For example, compounds of the indole family, such as 3-methyl indole (skatole) can be used as odor enhancers.

In another aspect the invention provides a method for riot control comprising obtaining a non-lethal riot control composition, which comprises the repellent composition of the invention and applying the composition on a rioting crowd. The composition can be applied on the crowd by diluting the composition in water and spraying the composition by a water gun. In other embodiments the composition can be applied in a projectile by a gun, in hand held canister and thrown as grenades.

EXAMPLE 1 13501-IL Lion feces collected on the day they were excreted, put in a closed container and frozen, were obtained from The Tisch Family Zoological Gardens in Jerusalem, also known as the Jerusalem Biblical Zoo. The raw feces contained portions of undigested meat. The feces were placed in an air tight vessel and frozen overnight at -18 °C. The following day the feces were thawed and dispersed around a residential backyard that was damaged by intruding wild boars. The wild boars were observed to notice the lion feces and deter from the lawn.

This example demonstrates that lion feces are capable of deterring wild boars.

EXAMPLE 2 The volatile compounds profiles of fresh predator feces were determined by a headspace GC-MS analysis conducted by the Daren Laboratories, Nes-Ziona Israel.

An approximate amount of 0.5g predator feces was placed in a 2 ml vial with polydimethylsiloxane septum. The samples were incubated at the required temperature as directed. The 10 μl samples were extracted and injected to the GC. The GC−MS analyses were performed on an Agilent 6890/5977A GC-MS system equipped with Agilent 30 m × 0.25 mm i.d. HP-5MS UI column (5% Phenyl/Methylpolysiloxane, 0.25 μm film thickness). The carrier gas was helium (99.999%) at a constant flow rate of 1.2 mL/min. The GC conditions were as follows: injector temperature 180 °C in splitless mode; initial oven temperature 40 °C hold for 3 min and increased to 250 °C at a rate of 20 °C/min with 5 min hold time. MS was performed in the EI positive ion mode, using the electron energy of 70 eV. Transfer line temperature and ion source temperature were maintained at 250°C both. MS data were collected in full-scan mode (m/z 20−400) and analyzed with Agilent Chemstation software. 13501-IL EXAMPLE 3 The volatile compounds profile of two batches of fresh lion feces were that were obtained from The Jerusalem Biblical Zoo was determined according to the procedure detailed in Example 2.

The list of volatile compounds and their relative tics in the headspace GC-MS analysis of each of the two batches of feces are presented in Table 1 under "Lion Feces 1" and "Lion Feces 2".

Table 1.

Lion Feces (relative intensity) Lion Feces (relative intensity) Repellent (% w/w) Repellent 1A (% w/w) Repellent 1B (% w/w) Water 27.246 25. 25.32 25.Acetone 54.02 51.04 65.49.96 49.Triethylamine 0.091 0.0.09 0.Butan-2-one 3.703 4.25 5.4.38 5.Acetaldehyde 2.11 0.2.17 0.Isovaleraldehyde 1.468 1.52 2.1.57 1.Acetic acid 1.424 1.133 1.1.16 1.delta-valerolactam 1.49 0.1.53 1.Isopentyl alcohol 0.2 0.0.22 0.Dimethyl disulfide 0.108 0.28 0.0.00 0.Propionic acid 0.709 0.99 1.1.02 1.Pentanol 0.4 0.0.20 0.Isobutyric acid 1.483 1.23 2.1.27 0.Butyric acid 2.323 2.11 4.2.17 2.4-methylvaleric acid 0.03 0.0.03 0.Pivaldehyde 1.51 0.1.56 1.Isovaleric acid 1.846 1.73 3.1.78 2.2-Methylbutyric acid 1.154 1.1 2.1.13 1.Valeric acid 1.927 1.88 4.1.94 2.Isopropyl valerate 0.026 0.0422 0.0.00 0.Propyl 2-methylbutanoate 0.0 0.0.04 0.

Propyl valerate 0.0 0.0.00 0.octane thiol 1.08 0.1.11 1.37 13501-IL Isobutylacetic acid 0.022 0.012 0.0.01 0.Benzaldehyde 0.084 0.11 0.0.00 0.2,5-dimethylpiperazine 0.13 0.0.13 0.

Phenol 0.752 0.89 1.0.92 0.Hexyl pentanoate 0.021 0.019 0.0.00 0.Octanal 0.008 0.014 0.0.02 0.Thioglycolic acid 0.08 0.0.00 0.Cresol 0.905 1.05 2.0.16 0.Nonanal 0.019 0.025 0.0.03 0.2-Piperidone 0.025 0.029 0.0.00 0.Indole 0.049 0.062 0.0.08 0.

EXAMPLE 4 Repellent composition no. 1 was prepared by mixing all the compound that appear in the first sample volatile compounds analysis that was determined in Example 3. Repellent compositions nos. 1A and 1B were prepared by mixing compounds that appear in the either the first or second sample of volatile compounds analysis that were determined in Example 3, while excluding compounds which may be toxic such as methyl disulfide or suspect carcinogenic. The compounds were obtained from Sigma, Aldrich, Acros and Fischer. The amounts of each compound are closely equivalent to the tic molar ratio of the GC-MS analysis. Table 1 summarizes the weight to weight ratio of all organic ingredients of the compositions. The compositions were then diluted with water to obtain an aqueous solution.

EXAMPLE 5 Repellent composition 1 that was prepared according to Example 4 was sprayed in a designated area of a backyard infested by wild boars. The wild boars as well as the guard dogs were deterred from the area to which the repellent composition was applied. After 15 minutes, some of the ingredients evaporated and the composition lost its effectiveness. 13501-IL This example demonstrates that the lion feces mimic composition Repellent 1 is effective in repelling wild boars and dogs.

EXAMPLE 6 A test person approached an industrial facility inhabiting guard dogs without repellent composition 1 which prompted the dogs to bark extremely aggressively near the fence of the facility for a very long period of time even after leaving the area.

Repellent composition 1 was then applied on the cloths of the test person, and when the test person approached the facility again, the dogs began barking but as the test person got near the fence, the dogs were deterred from the fence and stopped barking.

This example demonstrates that the Lion feces mimic repellent composition 1 is effective in repelling dogs and attenuating their aggressiveness.

EXAMPLE 7 Approximately 100 ml of repellent composition 1 was sprayed over the cloths of a test person who approached the facility of Example 6 at night. The dogs approached the fence only after continuously kicking the fence but retreated back to the facility after getting near the fence.

After an hour the test person returned to the facility. The dogs barked from inside the facility but did not approach the fence.

A week after, wearing the same cloths the dogs did not bark or approach even after kicking the gate of the facility, which normally would result in a very aggressive response.

Three more days after – same attempt and same results. 13501-IL To check if the dogs just got used to the test person’s presence, the test person returned to the facility at the same hour with different cloths – the dogs responded very aggressively.

A visit to the facility two weeks later – the dogs were completely passive.

The results demonstrate that the Lions feces mimic repellent composition is extremely effective as a dog repellent and is capable of attenuating their aggressiveness even two weeks after the composition was applied on the clothing.

EXAMPLE 8 Approximately 50 ml of repellent composition 1 were applied to cotton wool in a plastic box that was placed in a 1 m X 1 m cage containing two freely moving mature rats in the Jerusalem Biblical Zoo. The rats became still and did not move for several hours even when they were touched with a stick. After several hours, the plastic box that contained the soaked cotton wool was taken out of the cage and after a while the rats returned to normal function.

The example demonstrates that the repellent composition of the invention is also effective against rats.

EXAMPLE 9 Repellant compositions 1A and/or 1B can be tested in a similar manner as Repellent composition 1 was tested in any one of Examples 5 to 8.

EXAMPLE 10 The volatile compounds profile of fresh cat feces were that were obtained from domestic cats was determined according to the procedure detailed in Example 2. 13501-IL The list of volatile compounds and their relative tics in the headspace GC-MS analysis are presented in Table 2.

Table 2.

Cat Feces (relative intensity) Repellent 2 (% w/w) Acetone 12 22.Butan-2-one 2 4.Acetaldehyde 12 16.Methanol 3 3.Formamide 0.11 0.Acetic acid 6 11.isopropyl alcohol 2 3.Isopentyl alcohol 1.5 4.3-Methyl-2-buten-1-thiol 1.4 4.Butyric acid 0.11 0.Pivaldehyde 0.8 2.3-Methyl-3-buten-1-ol 0.22 0.2-Methylbutyric acid 0.4 1.Acetamide 0.11 0.Valeric acid 0.8 2.octane thiol 1.1 5.Isobutylacetic acid 0.8 2.Benzaldehyde 1.1 3.Dimethyl sulfone 0.9 2.Methylphenol 0.9 3.Octanal 0.8 3.Thioglycolic acid 0.08 0.

EXAMPLE 11 Repellent composition 2 was poured on and around rodents’ food that was placed in a dish in an aquarium accommodating a single mouse. Before the composition was applied the mice moved freely around the aquarium. After the application of the repellant composition, the mouse did not get near the dish for several hours, and from 13501-IL time to time it stood on its back feet and made attempts to escape the aquarium from distal sides to the food.

In a separate aquarium containing three mice the same food was placed in one corner of the aquarium and the repellent composition 2 was applied at an opposite corner. The mice ate the food and did not get near the area to which the composition was applied.

These experiments demonstrate the usefulness of the cat feces mimic composition as a mice repellent.

EXAMPLE 12 Repellent Composition 2 was applied to pedding material that was placed in a bathtub containing mice. After making redundant attempts to escape the bathtub, the mice became apathetic and refrained from any movement for hours, possibly pretending to be dead.

These experiments demonstrate the usefulness of the cat feces mimic composition as a mice repellent.

EXAMPLE 13 Assessment of the effectiveness of a predator (e.g. cat) feces mimic composition according to the invention can be conducted by obtaining two groups of prey animals (e.g. mice), in each group an even number of male and female prey animals, and placing group of prey animals in a separate open area covered with cameras. In one area the cat feces mimic composition can be applied at a specific location and in the other no composition is applied. Observing differences in the behavioral patterns between the two group can demonstrate the usefulness and effectiveness of the examined composition. 13501-IL EXAMPLE 14 A batch of fresh tiger feces that were obtained from The Jerusalem Biblical Zoo. The volatile compounds profile of the tiger feces was determined mutatis mutandis according to the procedure detailed in Example 2.

Repellent composition no. 3 was prepared by mixing compounds that appear in a volatile compounds analysis excluding those which are considered to be toxic and/or carcinogenic. The composition was then diluted with water to obtain an aqueous solution (Composition 1). Materials were obtained from Sigma, Aldrich, Acros and Fischer. The amounts of each compound are equivalent to the tic molar ratio of the GC-MS analysis. Table 3 summarizes the relative amounts and weight to weight ratio out of the total weight of the composition.

Table Repellent (mg) Repellent (%w/w) Headspace water 500 57.Acetone 141 16.Butan-2-one 2.Isovaleraldehyde 12.2 1.Isobutyric acid 1.4-methylvaleric acid 0.45 0.Pivaldehyde 18.9 2.Isovaleric acid 21.1 2.Valeric acid 22.4 2.Isopropyl valerate 0.21 0.Isobutylacetic acid 0.4 0.4-hydroxypentanone 13.2 1.argenine methyl ester 0.4 0.octanol 9.2,3-dihydroxybenzoic acid 8.8 1.2,6,11,15, tetramethyltetradecane 1.2 0.2,6,10-trimethyltetradecane 0.13 0.2-methyl eicosane 0.19 0.di-tert-dodecyldodecane 0.15 0.02 13501-IL 2,6,11,15, tetramethylhexadecane 0.19 0.heptamethyldodecane* 0.22 0.11,13-dimethyltetradecanol acetate 1.4 0.cholesterol acetate 0.04 0.dodecane thiol 7.4 0. Total 864.98 1*several isomers EXAMPLE 15 Repellent composition 4 mimicking tiger feces was prepared in a similar manner as repellent composition 3 as detailed in Example 14. Table 4 summarizes the relative amounts and weight to weight ratio out of the total weight of the composition.

Table 4.

Repellent (mg) Repellent (%w/w) Headspace water 50 53.

Acetone 14.1 14.Butan-2-one 2.2 2.

Octanal 1.22 1.

Nonal 1.45 1.Isobutyric acid 1.1 1. 4-methylvaleric acid 0.045 0. 3-methylbutyraldehyde 1.89 2.Isovaleric acid 2.11 2.

Valeric acid 2.24 2.

Isopropyl valerate 0.021 0.Butyric acid 0.04 0. 4-hydroxypentanone 1.32 1.40 13501-IL pentol 0.04 0.octanol 8.2 8. dodecane thiol 0.74 0.Octane thiol 3.2 3.

Isoamyl alcohol 4.2 4. 94.116 1 EXAMPLE 16 Cotton wool soaked with 4 ml of the tiger feces mimic composition that is characterized in Example 14 (Repellant 4) was placed in three cardboard boxes which were dispersed in three separate location in a backyard of a house infested with rock hyrax. The latter disappeared for the following ten days.

EXAMPLE 17 A canine feces mimic composition can be prepared mutatis mutandis in a similar manner as the composition detailed in preceding examples.

Claims (41)

13401-IL1 291535/ CLAIMS

1. A repellent composition comprising a mixture of volatile compounds selected from compounds of a volatile compounds profile of predator feces, the compounds of the volatile compounds profile comprising: at least one of triethylamine, δ-valerolactam and 2,5-dimethylpiperazine or salts thereof; at least one linear, branched or cyclic, aliphatic or aromatic C 2 to C 9 aldehyde; at least one linear, branched or cyclic, saturated or unsaturated aliphatic C 1 to C 9 alcohol; at least one linear or branched C 2 to C 8 aliphatic carboxylic acid optionally having a sulfur atom, or linear or branched C 3 to C 8 alkyl ester thereof; at least one linear saturated or unsaturated C 2 to C 8 organosulfur compound having one to two sulfur atoms and optionally one to two oxygen atoms; optionally at least one optionally alkyl substituted C 6 to C 8 aromatic alcohol; and optionally at least one ketone selected from acetone and methyl ethyl ketone.

2. The repellent composition according to claim 1 wherein the predator feces are selected from feline feces, canid feces or a mixture thereof.

3. The repellent composition according to claim 1 or 2 wherein the volatile compounds profile is elucidated by an analytical method selected from headspace GC-MS analysis and solid phase microextraction (SPME) followed by GC-MS.

4. The repellent composition according to claims 1 to 3 comprising at least 75% of the compounds that are present in the volatile compounds profile of the predator feces. 13401-IL1 291535/

5. The repellent composition according to any one of claims 1 to 3 wherein the feline feces are selected from cat feces, caracal feces, leopard feces, lion feces, tiger feces, tigris feces, panther feces, cheetah feces or a mixture thereof.

6. The repellent composition according to any one of claims 1 to 4 wherein the canid feces are selected from dog feces, coyote feces, wolf feces, fox feces, bear feces, or a mixture thereof.

7. The repellent composition according to any one of claims 1 to 5 wherein the volatile compounds profile being obtainable by collection of the volatile materials emitted from predator feces.

8. The repellent composition according to any one of claims 1 to 7 comprising a mixture of volatile compounds corresponding to a volatile compounds profile of predator feces and having a LD 50 oral rat value lower than 200, 500 or 10mg/KG body weight.

9. The repellent composition according to any one of claims 1 to 8 comprising: – 25 % w/w out of the total weight if the composition of at least one linear, branched or cyclic, aliphatic or aromatic C 2 to C 9 aldehyde, 0.5 – 10 % w/w out of the total weight if the composition of at least one linear, branched or cyclic, C 1 to C 8 aliphatic alcohol, – 20 % w/w of at least one optionally alkyl substituted aromatic alcohol having to 7 carbon atoms, – 80 % w/w out of the total weight if the composition of at least one linear or branched aliphatic C 3 to C 8 carboxylic acid optionally having a sulfur atom, or linear or branched C 3 to C 6 alkyl ester thereof, 0.1 – 15 % w/w out of the total weight if the composition of at least one linear C 2 to C 8 organosulfur compound having one to two sulfur atoms, and – 75 % w/w out of the total weight if the composition at least one of acetone and methylethylketone. 13401-IL1 291535/

10. The repellent composition according to any one of claims 1 to 9 comprising at least one of acetone and methyl ethyl ketone.

11. The repellent composition according to any one of claims 1 to 10 wherein the at least one aldehyde is selected from acetaldehyde, isovaleraldehyde, pivaldehyde, benzaldehyde, octanal and nonal.

12. The repellent composition according to any one of claims 1 to 11 wherein the at least one aliphatic alcohol is selected from methanol, iso-pentyl alcohol, pentanol, 4-hydroxy-pentanone, octanol and 3-methyl-3-buten-1-ol.

13. The repellent composition according to any one of claims 1 to 12 wherein the at least one aromatic alcohol is selected from cresol and phenol.

14. The repellent composition according to any one of claims 1 to 13 wherein the at least one carboxylic acid is selected from acetic acid, butyric acid, 4-methyl valeric acid, valeric acid and the alkyl groups of the esters are selected from propyl, iso-propyl and hexyl.

15. The repellent composition according to any one of claims 1 to 14 wherein the at least one heteroaliphatic compound selected from methyl disulfide, 2,5-dimethyl piperazine and octane thiol.

16. The repellent composition according to any one of claims 1 to 15 comprising at least one of C 1 to C 8 aliphatic alcohol.

17. The repellent composition according to any one of claims 1 to 16 comprising isovaleraldehyde, acetic acid, methyl disulfide, propionic acid, isobutyric acid, butyric acid, isovaleric acid, 2-methylbutyric acid, valeric acid, isopropyl valerate, isobutylacetic acid, benzaldehyde, phenol, hexyl pentanoate, octanal, cresol, nonanal, 2-piperidone, and indole.

18. The repellent composition according to claim 17 further comprising isopentanol, pentanol, propyl 2-methylbutanoate and propyl valerate. 13401-IL1 291535/

19. The repellent composition according to claim 18 wherein the predator feces are lion feces comprising: – 25 % w/w of at least one linear, branched or cyclic, aliphatic or aromatic C to C 9 aldehyde, 0.5 – 10 % w/w of at least one linear, branched or cyclic, C 3 to C 7 aliphatic alcohol, – 20 % w/w of at least one optionally alkyl substituted C 6 to C 7 aromatic alcohol, – 80 % w/w of at least one linear or branched aliphatic C 2 to C 8 carboxylic acid optionally having a sulfur atom, or linear or branched C 3 to C 6 alkyl ester thereof, 0.1 – 15 % w/w of at least one linear C 2 to C 8 organosulfur compound having and one to two sulfur atoms, and – 5 % w/w of at least one C 8 heteroaromatic compound having one nitrogen atom, 0.01 – 1 % w/w of at least one lactam and – 75 % w/w at least one of acetone and methylethylketone.

20. The repellent composition according to any one of claims 1 to 18 being formulated as an aqueous solution, oil in water emulsion, water in oil emulsion or aqueous suspension wherein the volume of the composition out of the total volume of the formulation is between 1-90 % V/V.

21. The repellent composition according to claim 18 comprising: – 9 % w/w isovaleraldehyde, – 6 % w/w acetic acid, – 2 % w/w isopentyl alcohol, 0.5 – 1.5 % w/w methyl disulfide, – 4 % w/w propionic acid, 13401-IL1 291535/ 0 – 3 % w/w pentanol, – 10 % w/w isobutyric acid, – 15 % w/w butyric acid, – 14 % w/w isovaleric acid, – 9 % w/w 2-methylbutyric acid, – 15 % w/w valeric acid, 0.1 – 0.5 % w/w isopropyl valerate, – 0.1 % w/w propyl 2-methylbutanoate, – 0.1 % w/w propyl valerate, 0.2 – 0.3 % w/w isobutylacetic acid, 0.5 – 1.0 % w/w benzaldehyde, 4.5 – 5 % w/w phenol, 0.2 – 0.3 % w/w hexyl pentanoate, 0.1 % w/w octanal, – 7 % w/w cresol, 0.2 % w/w nonanal, 0.2 – 8 % w/w 2-piperidone, and 0.4 % w/w indole out of the total weight of the composition.

22. The repellent composition according to claim 21 being formulated with 60-% w/w at least one of acetone and methyl ethyl ketone.

23. The repellent composition according to any one of claims 19 to 22 further comprising at least one of a C 2 – C 6 secondary amine and a C 6 – C 7 optionally alkyl substituted aromatic alcohol.

24. The repellent composition according to claim 1 wherein the predator feces are tiger feces, the composition comprising: 1- 20 % w/w acetone, 1 – 5 % w/w butanone, 1 – 2 % w/w octanal, 1 – 2 % w/w nonal, 1 – 2 % w/w isobutyric acid, 0.01 – 0.5 % w/w 4-methylvaleric acid, 1 – 2 % w/w 3- methyl butyraldehyde 13401-IL1 291535/ isovaleraldehyde, 1 – 3 % w/w isovaleric acid, 1 – 3 % w/w valeric acid, 0.01 – 0.5 % w/w isopropyl valerate, 0.01 – 0.5 % w/w butyric acid, 1 – 3 % w/w 4-hydroxypentanone, 0.01 – 0.5 % w/w pentanol, 1 to 5 % w/w C 8 to C 12 aliphatic thiols, and 3 – 6% isoamyl alcohol out of the total weight of the composition.

25. The repellent composition according to claim24 further comprising an extender.

26. The repellent composition according to claim or 25 wherein the extender is selected from glycol, glycerol, ethylene glycol, polyethylene glycol and mixtures thereof.

27. The repellent composition according to any one of claims 1 to 26 being formulated as an aerosol, emulsion, solution, cream, lotion or gel.

28. An animal repellent composition comprising the repellent composition as defined in any one of claims 1 to 27.

29. The animal repellent composition according to claim 28 wherein the animal is a mammal.

30. The animal repellent composition according to claim 28 or 29 wherein the predator feces are lion feces and the animal is a canid selected from a dog, moose, deer and wild boar.

31. The animal repellent composition according to claim 28 or 29 wherein the predator feces are leopard feces and the animal is a rock hyrax.

32. The animal repellent composition according to any one of claims 28 or wherein the predator feces are cat feces and the animal is a rodent.

33. The animal repellent composition according to claim 32 wherein the composition comprising: acetaldehyde, methanol, formamide, acetic acid, isopropyl alcohol, isopentyl alcohol, isobutyric acid, 3-methyl-buten-1-thiol, butyric acid pivaldehyde, 3-methyl-buten-1-ol, 2-methylbutyric acid, acetamide, valeric acid, octane thiol, 13401-IL1 291535/ isobutylacetic acid, benzaldehyde, dimethyl sulfone, octanal, cresol, and thioglycolic acid.

34. The animal repellent composition according to any one of claims 28 to further comprising an additional animal repellent active ingredient.

35. The animal repellent composition according to any one of claims 28 to 34 being formulated as an aerosol, emulsion, solution, cream, lotion or gel.

36. A method for repelling animals comprising applying the composition defined in claim 28 or 35 to an area or article from which the animals are meant to be deterred.

37. The method according to claim 36 wherein the composition is applied to a subject from which the animals are meant to be deterred.

38. A riot control composition comprising the repellent composition as defined in any one of claims 1 to 27.

39. The riot control composition according to claim 38 further comprising at least one additional malodor active ingredient.

40. An article comprising the riot control composition as defined in any one of claims 38 to 39.

41. The article according to claim 40 being one of a malodor grenade, a water cannon malodor cylinder, and a water cannon reservoir tank. For The Applicant: Dr. Lior Eshdat License No. 391