Arthropod control composition

Abstract

The present invention relates to arthropod control compositions, methods and uses for controlling arthropods, and consumer products comprising the arthropod control compositions.

Description

[Technical Field]

[0001] The present invention relates to arthropod control compositions, methods and uses for controlling arthropods, and consumer products comprising the arthropod control compositions.

[0002] Background technology Many mammals, including humans, suffer from the effects of arthropods. Some arthropods, such as mosquitoes and ticks, bite and subsequently cause itching, disease, and / or the transmission of pathogens, or may be the cause of other diseases and / or conditions, making them undesirable for mammals, particularly vertebrates such as human subjects. Similarly, other pests indirectly affect human activities or societies by feeding on, infesting, or destroying plant materials used as food, feed, or raw materials. Still other pests are responsible for the destruction or weakening of furniture or structures used or constructed by humans. These damages may be directly attributable to arthropods or due to their ability to spread the bacteria that cause such problems.

[0003] The arthropod control composition contains an active substance and, when applied to the skin, clothing, or other surface, can prevent arthropods from landing on or climbing on the surface. The arthropod control agent helps prevent and control the occurrence of arthropod-borne diseases such as malaria.

[0004] However, some of the known arthropod control agents and compositions have certain drawbacks because they may have negative effects, i.e., negative olfactory properties such as no odor or a foul odor, or only weak arthropod control, especially arthropod repellent properties.

[0005] There is a need to identify additional compounds that allow for efficient arthropod control. [Brief explanation of the drawings]

[0006] [Figure 1]Figure 1 shows the percentage of repellency of Aedes aegypti mosquitoes landing on worm bodies attracted by 40 μg of C10 γ-lactones of different chain lengths. Each point represents the repellency of mosquitoes attracted by saturated γ-lactones (black circles) or unsaturated γ-lactones (gray squares). The average number of mosquitoes landing on worm bodies attracted by solvent alone (ethanol) was equal to 66.7 ± 7.7 times in 2 min. [Figure 2] Figure 1 shows the percentage of repellency of Aedes aegypti mosquitoes landing on worm bodies attracted by different concentrations of C10 γ-lactone. Each point represents the response to saturated C10 γ-lactone 5-hexyloxolan-2-one (black circles) and unsaturated C10 γ-lactone 5-hex-3-enyloxolan-2-one (gray squares) at 13 different concentrations. The average number of mosquitoes landing on worm bodies attracted by solvent alone (ethanol) was equal to 62.7 ± 1.2 times in 2 min. [Figure 3] Figure 1 shows the percentage of repellency of Aedes aegypti mosquitoes landing on warm bodies attracted by different concentrations of C10 δ-lactone. Each point represents the response to the saturated C10 δ-lactone 6-pentyloxan-2-one (black circles) and the unsaturated C10 δ-lactones 6-pent-2-enyloxan-2-one (dark gray squares) and 6-pent-3-enyloxan-2-one (light gray triangles) at 13 different concentrations. The average number of mosquitoes landing on warm bodies attracted by the solvent alone (ethanol) was equal to 69.7 ± 5.1 times over 2 min. [Figure 4]Figure 1 shows the percentage of repellency of Anopheles gambiae mosquitoes landing on warm bodies attracted by different concentrations of C10 δ-lactone. Each point represents the response to the saturated C10 δ-lactone 6-pentyloxan-2-one (black circles) and the unsaturated C10 δ-lactones 6-pent-2-enyloxan-2-one (dark gray squares) and 6-pent-3-enyloxan-2-one (light gray triangles) at 13 different concentrations. The average number of mosquitoes landing on warm bodies attracted by the solvent alone (ethanol) was equal to 69.7 ± 5.1 times in 2 min. [Figure 5] Mosquitoes, Aedes aegypti, landed on human forearms treated with C10 δ-lactone (20% in ethanol) at different time points after application. Each point represents the mean ± SD response to the saturated C10 δ-lactone 6-pentyloxan-2-one (black circles) and the unsaturated C10 δ-lactones 6-pent-2-enyloxan-2-one (dark gray squares) and 6-pent-3-enyloxan-2-one (light gray triangles). The untreated arm received 374, 377, and 472 mosquito landings during the 3-minute test period for the three test compounds, respectively. For human volunteers, testing was stopped when repellency fell below 90% for all volunteers.

[0007] MODE FOR CARRYING OUT THE INVENTION The present invention provides a compound selected from the group consisting of the following formulas: [ka] In the formula, R1 is hydrogen or a linear or branched C1-C1 alkyl group having 0 to 2 unsaturations. 15 represents a hydrocarbon group, wherein R2 is hydrogen or a linear or branched C1-C1 alkyl group having 0-3 unsaturations. 15 represents a hydrocarbon group, or wherein R1 and R2 together form a cycloalkyl, cycloalkenyl, or aryl ring optionally substituted with one or more methyl or ethyl groups; In the formula, n is an integer of 1 to 3, wherein R3 is hydrogen or a linear or branched C1-C1 alkyl group having 0-3 unsaturations. 15 represents a hydrocarbon group, Arthropod control compositions are provided that include compounds in which the dotted line in formula (I) indicates that the double bond can be present at any position on the lactone ring.

[0008] The term "hydrocarbon group" refers to its usual meaning in the art, i.e., a group consisting of carbon and hydrogen atoms.

[0009] The term "unsaturated" refers to the presence of a carbon-carbon double or triple bond in the lactone side chain.

[0010] According to the present invention, R1 and R2 may together form a cycloalkyl, cycloalkenyl, or aryl ring optionally substituted with one or more methyl or ethyl groups, in which case the R1 and R2 groups in formula (I) are preferably attached to adjacent carbon atoms.

[0011] In certain embodiments, R1 and R2 together do not form an aryl ring, and in particular do not form a phenyl ring.

[0012] According to the present invention, the dotted line in formula (I) indicates that a double bond may be present at any position on the lactone ring. Preferably, the double bond is present at a position adjacent to the carbonyl carbon atom. In certain embodiments, there is no double bond in the lactone ring.

[0013] The term "optionally" is understood to mean that a particular group that is optionally substituted may or may not be substituted with a particular chemical group, for example, a methyl or ethyl group.

[0014] In certain embodiments, the compound is of formula (I): In another embodiment, the compound is of formula (II):

[0015] In certain embodiments, n is an integer of 1 or 2, preferably 1. In other embodiments, n is an integer of 2.

[0016] In certain embodiments, R1 and R2, R1 and R3, or R2 and R3 are present on the same carbon atom in formula (I), preferably the carbon atom adjacent to the ring oxygen atom. In such embodiments, the R groups present on the same carbon atom are linear or branched C1-C groups with no unsaturation. 15 A hydrocarbon group is preferred.

[0017] In certain embodiments, at least one of R1-R3 is a straight chain C1-C6 alkyl group having at least one unsaturation. 15 It represents a hydrocarbon group, preferably a straight-chain C4 to C8 hydrocarbon group having at least one unsaturation.

[0018] In certain embodiments, at least one of R1-R3 is a straight chain C1-C1 alkyl group having one unsaturation. 15 It represents a hydrocarbon group, preferably a linear C4 to C8 hydrocarbon group having one unsaturation.

[0019] In certain embodiments, at least one of R1-R3 is a straight chain C1-C6 alkyl group having two unsaturations. 15 It represents a hydrocarbon group, preferably a linear C4 to C8 hydrocarbon group having two unsaturations.

[0020] In certain embodiments, none of R1-R3 represents a branched C4-C5 hydrocarbon group having at least one unsaturation.

[0021] In certain embodiments, at least one of R1-R3 is a straight chain or branched C1-C1 alkyl group having at least one unsaturation. 15 Hydrocarbon groups, preferably linear or branched C2-C with at least one unsaturation 15Hydrocarbon groups, more preferably linear or branched C2-C3 or C6-C6 with at least one unsaturation 15 Hydrocarbon groups, most preferably straight or branched C2-C3 or C6-C9 or C with at least one unsaturation 11 ~C 15 represents a hydrocarbon group.

[0022] In certain embodiments, at least one of R1-R3 is a straight-chain or branched C1-C6 alkyl group having two or three unsaturations. 15 Hydrocarbon groups, preferably linear or branched C2-C with two or three unsaturations 15 Hydrocarbon groups, more preferably linear or branched C2 to C9 or C with two or three unsaturations 11 ~C 15 Represents a hydrocarbon group. In particular, R2 is a linear or branched C1-C2 hydrocarbon group having two or three unsaturations. 15 Hydrocarbon groups, preferably linear or branched C2-C with two or three unsaturations 15 Hydrocarbon groups, more preferably linear or branched C2 to C9 or C with two or three unsaturations 11 ~C 15 represents a hydrocarbon group.

[0023] In certain embodiments, R1 to R3 are all C 10 does not represent a hydrocarbon group. In particular, R2 is C 10 It does not represent a hydrocarbon group.

[0024] In certain embodiments, none of R1 to R3 represents a decenyl group, and in particular, R2 does not represent a decenyl group.

[0025] In certain embodiments, none of R1 to R3 represents a dec-1-enyl group, and in particular, R2 does not represent a dec-1-enyl group.

[0026] In certain embodiments, the compound of formula (I) has the formula [ka] is selected from the group consisting of:

[0027] In this embodiment, R1 and R3 are hydrogen. The dotted lines in formulas (III) and (IV) indicate that the double bond may be present at any position on the lactone ring. Preferably, the double bond is present at the position adjacent to the carbonyl carbon atom.

[0028] In certain embodiments, the compound of formula (I) is of formula (III). In one embodiment, a double bond is present in the lactone ring of formula (III). In another embodiment, no double bond is present in the lactone ring of formula (III). Preferably, no double bond is present in the lactone ring of formula (IV).

[0029] In certain embodiments, the compound of formula (I) is of formula (IV). In one embodiment, a double bond is present in the lactone ring of formula (IV). In another embodiment, no double bond is present in the lactone ring of formula (IV). Preferably, no double bond is present in the lactone ring of formula (IV).

[0030] In certain embodiments, the compound of formula (I) has the formula [ka] is selected from the group consisting of:

[0031] In this embodiment, R1 and R3 are hydrogen. In this embodiment, the compound does not contain a double bond in the lactone ring.

[0032] In certain embodiments, the compound of formula (I) is of formula (V):

[0033] In certain embodiments, the compound of formula (I) is of formula (VI):

[0034] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C1-C1 alkyl group having 1-3 unsaturations. 15 represents a hydrocarbon group.

[0035] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight chain or branched C2-C6 alkyl group having 1-3 unsaturations. 15 represents a hydrocarbon group.

[0036] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight chain C2-C6 alkyl group having 1-3 unsaturations. 15 represents a hydrocarbon group.

[0037] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight chain or branched C1-C1 15 represents a hydrocarbon group.

[0038] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight chain or branched C2-C6 alkyl group having one unsaturation. 15 represents a hydrocarbon group.

[0039] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight chain or branched C1-C1 15 represents a hydrocarbon group.

[0040] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight chain or branched C2-C3 alkyl group having two unsaturations. 15 represents a hydrocarbon group.

[0041] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C1-C1 alkyl group having three unsaturations. 15 represents a hydrocarbon group.

[0042] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight chain or branched C2-C3 alkyl group having three unsaturations. 15 represents a hydrocarbon group.

[0043] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C2-C9 or C 11 ~C 15 represents a hydrocarbon group.

[0044] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C2-C9 or C 11 ~C 15 represents a hydrocarbon group.

[0045] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C2-C9 or C 11 ~C 15 represents a hydrocarbon group.

[0046] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C2-C9 or C 11 ~C 15 represents a hydrocarbon group.

[0047] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C2-C3, C6-C9 or C 11 ~C 15 represents a hydrocarbon group.

[0048] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C2-C3, C6-C9 or C 11 ~C 15 represents a hydrocarbon group.

[0049] In certain embodiments, R1 and R3 are hydrogen and R2 is a linear or branched C2-C3, C6-C9 or C 11 ~C 15 represents a hydrocarbon group.

[0050] In certain embodiments, R1 and R3 are hydrogen and R2 is a linear or branched C2-C3, C6-C9 or C 11 ~C 15 represents a hydrocarbon group.

[0051] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C8-C8 alkyl group having 1-3 unsaturations. 12 represents a hydrocarbon group.

[0052] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight chain or branched C8-C8 alkyl group having one unsaturation. 12 represents a hydrocarbon group.

[0053] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C8-C8 alkyl group having two unsaturations. 12 represents a hydrocarbon group.

[0054] In certain embodiments, R1 and R3 are hydrogen and R2 is a linear or branched C8-C8 alkyl group having three unsaturations. 12 represents a hydrocarbon group.

[0055] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C8-C8 alkyl group having 1-3 unsaturations. 12 represents a hydrocarbon group.

[0056] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C4-C6 alkyl group having 1-3 unsaturations. 10 It represents a hydrocarbon group, preferably a C4 to C8 hydrocarbon group.

[0057] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C4-C 10 It represents a hydrocarbon group, preferably a C4 to C8 hydrocarbon group.

[0058] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight chain or branched C4-C 10 It represents a hydrocarbon group, preferably a C4 to C8 hydrocarbon group.

[0059] In certain embodiments, R1 and R3 are hydrogen and R2 is a linear or branched C6-C6 alkyl group having three unsaturations. 10 It represents a hydrocarbon group, preferably a C4 to C8 hydrocarbon group.

[0060] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C 10 represents a hydrocarbon group.

[0061] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C 10 represents a hydrocarbon group.

[0062] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C 10 represents a hydrocarbon group.

[0063] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight or branched C 10 represents a hydrocarbon group.

[0064] In certain embodiments, R1 and R3 are hydrogen and R2 is a straight chain or branched C7-C 10 In other words, in this embodiment, R2 is a linear or branched C7-C 10 represents an alkyl group.

[0065] In certain embodiments, the compound is selected from the group consisting of 5-propyloxolan-2-one, 5-butyloxolan-2-one, 5-pentyloxolan-2-one, 5-hexyloxolan-2-one, and any combination thereof.

[0066] In a particular embodiment, the compound is 5-propyloxolan-2-one.

[0067] In a particular embodiment, the compound is 5-butyloxolan-2-one.

[0068] In a particular embodiment, the compound is 5-pentyloxolan-2-one.

[0069] In a particular embodiment, the compound is 5-hexyloxolan-2-one.

[0070] In a particular embodiment, the compound is 5-hexyl-5-methyloxolan-2-one.

[0071] In certain embodiments, the compound is 5-but-3-enyloxolan-2-one, 5-pent-3-enyloxolan-2-one, 2-pentyl-2H-furan-5-one, 5-hex-1-enyloxolan-2-one, 5-hex-2-enyloxolan-2-one, 5-hex-3-enyloxolan-2-one, 5-hex-4-enyloxolan-2-one, 5-hex-5-enyloxolan-2-one, 5-oct-1-enyloxolan-2-one, 5-oct-2-enyloxolan-2-one, 5-oct-3-enyloxolan-2-one, 5-oct-4-enyloxolan-2-one. , 5-[(E)-oct-5-enyl]oxolan-2-one, 5-[(Z)-oct-5-enyl]oxolan-2-one, 5-oct-6-enyloxolan-2-one, 5-oct-7-enyloxolan-2-one, 5-[(1E,5Z)-octa-1,5-dienyl]oxolan-2-one, 5-octa-1,5-dienyloxolan-2-one, 6-pent-2-enyloxan-2-one, 6-pent-3-enyloxan-2-one, 5-hexyl-5-methyloxolan-2-one, 1-oxaspiro[4.5]decan-2-one, and any combination thereof.

[0072] In certain embodiments, the compound is 5-but-3-enyloxolan-2-one, 5-pent-3-enyloxolan-2-one, 5-hex-1-enyloxolan-2-one, 5-hex-2-enyloxolan-2-one, 5-hex-3-enyloxolan-2-one, 5-hex-4-enyloxolan-2-one, 5-hex-5-enyloxolan-2-one, 5-oct-1-enyloxolan-2-one, 5-oct-2-enyloxolan-2-one, 5-oct-3-enyloxolan-2-one, 5-oct-4-enyloxolan-2-one, 5-oct ... 5-oct-1,5-dienyl]oxolan-2-one, 5-oct-2-enyloxolan-2-one, 5-[(E)-oct-5-enyl]oxolan-2-one, 5-[(Z)-oct-5-enyl]oxolan-2-one, 5-oct-6-enyloxolan-2-one, 5-oct-7-enyloxolan-2-one, 5-[(1E,5Z)-octa-1,5-dienyl]oxolan-2-one, 6-pent-2-enyloxan-2-one, 6-pent-3-enyloxan-2-one, 5-hexyl-5-methyloxolan-2-one, and any combination thereof.

[0073] In a particular embodiment, the compound is 5-but-3-enyloxolan-2-one.

[0074] In a particular embodiment, the compound is 5-pent-3-enyloxolan-2-one.

[0075] In a particular embodiment, the compound is 5-hex-1-enyloxolan-2-one.

[0076] In a particular embodiment, the compound is 5-hex-2-enyloxolan-2-one.

[0077] In a particular embodiment, the compound is 5-hex-3-enyloxolan-2-one.

[0078] In a particular embodiment, the compound is 5-hex-4-enyloxolan-2-one.

[0079] In a particular embodiment, the compound is 5-hex-5-enyloxolan-2-one.

[0080] In certain embodiments, the compound is a mixture of 5-hex-2-enyloxolan-2-one, 5-hex-3-enyloxolan-2-one, and 5-hex-4-enyloxolan-2-one, preferably 43% by weight 5-hex-2-enyloxolan-2-one, 25% by weight 5-hex-3-enyloxolan-2-one, and 32% by weight 5-hex-4-enyloxolan-2-one.

[0081] In a particular embodiment, the compound is 5-oct-1-enyloxolan-2-one.

[0082] In a particular embodiment, the compound is 5-oct-2-enyloxolan-2-one.

[0083] In a particular embodiment, the compound is 5-oct-3-enyloxolan-2-one.

[0084] In a particular embodiment, the compound is 5-[(E)-oct-5-enyl]oxolan-2-one.

[0085] In certain embodiments, the compound is 5-[(Z)-oct-5-enyl]oxolan-2-one.

[0086] In a particular embodiment, the compound is 5-oct-5-enyloxolan-2-one.

[0087] In a particular embodiment, the compound is 5-oct-6-enyloxolan-2-one.

[0088] In a particular embodiment, the compound is 5-oct-7-enyloxolan-2-one.

[0089] In a particular embodiment, the compound is 5-[(1E,5Z)-octa-1,5-dienyl]oxolan-2-one.

[0090] In a particular embodiment, the compound is 5-octa-1,5-dienyloxolan-2-one.

[0091] In certain embodiments, the compound is 6-pent-2-enyloxan-2-one.

[0092] In certain embodiments, the compound is 6-pent-3-enyloxan-2-one.

[0093] In certain embodiments, the compound is 5-but-3-enyloxolan-2-one, 5-pent-3-enyloxolan-2-one, 5-hex-1-enyloxolan-2-one, 5-hex-3-enyloxolan-2-one, 5-hex-5-enyloxolan-2-one, 5-oct-1-enyloxolan-2-one, 5-oct-2-enyloxolan-2-one, 5-oct-3-enyloxolan-2-one, 5-[(E)-oct-5-enyl]oxolan-2-one, ...pent-3-enyloxolan-2-one, 5-pent-3-enyloxolan-2-one, 5-pent-3-enyloxolan-2-one, 5-pent-3-enyloxolan-2-one, 5-pent-3-enyloxolan-2-one, 5-pent-3-enyloxolan-2-one, 5-pent-3-enyloxolan-2-one, 5-pent-3-enyloxolan-2-one, 5-pent-3-en solan-2-one, 5-[(Z)-oct-5-enyl]oxolan-2-one, 5-oct-6-enyloxolan-2-one, 5-oct-7-enyloxolan-2-one, 5-[(1E,5Z)-octa-1,5-dienyl]oxolan-2-one, 5-octa-1,5-dienyloxolan-2-one, 6-pent-2-enyloxan-2-one, 6-pent-3-enyloxan-2-one, and any combination thereof.

[0094] In certain embodiments, the compound is 5-but-3-enyloxolan-2-one. In certain embodiments, the compound is 5-pent-3-enyloxolan-2-one. In certain embodiments, the compound is 5-hex-1-enyloxolan-2-one. In certain embodiments, the compound is 5-hex-3-enyloxolan-2-one. In certain embodiments, the compound is 5-hex-5-enyloxolan-2-one. In certain embodiments, the compound is 5-oct-1-enyloxolan-2-one. In certain embodiments, the compound is 5-oct-2-enyloxolan-2-one. In certain embodiments, the compound is 5-oct-3-enyloxolan-2-one. In certain embodiments, the compound is 5-[(E)-oct-5-enyl]oxolan-2-one. In certain embodiments, the compound is 5-[(Z)-oct-5-enyl]oxolan-2-one. In certain embodiments, the compound is 5-oct-6-enyloxolan-2-one. In certain embodiments, the compound is 5-oct-7-enyloxolan-2-one. In certain embodiments, the compound is 5-[(1E,5Z)-octa-1,5-dienyl]oxolan-2-one. In certain embodiments, the compound is 6-pent-2-enyloxan-2-one. In certain embodiments, the compound is 6-pent-3-enyloxan-2-one.

[0095] In certain embodiments, the compound is selected from the group consisting of 5-hex-3-enyloxolan-2-one, 6-pent-2-enyloxan-2-one, and 6-pent-3-enyloxan-2-one, and any combination thereof.

[0096] According to any one of the above embodiments of the present invention, the compounds of Formulas (I) to (VI) may have several stereocenters, each of which may have two different stereochemistries (e.g., R or S). The compounds of Formulas (I) to (VI) may be in the form of pure enantiomers or mixtures of enantiomers or diastereoisomers. The compounds of Formulas (I) to (VI) may be in racemic or scalemic form. Thus, the compounds of Formulas (I) to (VI) may be in the form of a single stereoisomer or a composition of matter comprising or consisting of various stereoisomers. All structural and stereoisomers are encompassed by the above compounds and structures, respectively, particularly with regard to Z / E isomers in the case of unsaturation in the side chain of the lactone ring. Thus, unless explicitly indicated, all Z / E isomers are encompassed. Indeed, the compounds containing unsaturation may be in the form of their E or Z isomers or mixtures thereof. In particular, the compounds according to the above formulae may be in the form of a mixture of isomers E and Z, with isomer E representing at least 50% of the total mixture, or at least 75% (i.e. the mixture E / Z is comprised between 75 / 25 and 100 / 0). The compounds of formulae (I) to (VI) may also be pure enantiomers or diastereomers.

[0097] In certain embodiments, the 5-hex-3-enyloxolan-2-one is (Z)-5-hex-3-enyloxolan-2-one.

[0098] In certain embodiments, the 6-pent-2-enyloxan-2-one is (6R)-(Z)-6-pent-2-enyloxan-2-one or (6S)-(Z)-6-pent-2-enyloxan-2-one.

[0099] In certain embodiments, the 6-pent-3-enyloxan-2-one is (E)-6-pent-3-enyloxan-2-one.

[0100] In certain embodiments, the compound is 1-oxaspiro[4.5]decan-2-one.

[0101] In certain embodiments, the compound is selected from the following group of compounds and any combination thereof: [Table 1-1] [Table 1-2]

[0102] In certain embodiments, the compound is selected from the following group of compound structures and any combination thereof: [Table 2-1] [Table 2-2] [Table 2-3] [Table 2-4] [Table 2-5] [Table 2-6] [Table 2-7] [Table 2-8] [Table 2-9] [Table 2-10] [Table 2-11]

[0103] In certain embodiments, the arthropod control composition has good hedonic properties.

[0104] The term "arthropod" has its usual meaning to those skilled in the art. Arthropods include invertebrates, such as insects, arachnids, and crustaceans, which have segmented bodies and jointed appendages. Arthropods typically have a chitinous exoskeleton that is molted at intervals, and a dorsal anterior brain connected to a ventral chain of ganglia.

[0105] Arthropods in the understanding of the present invention refer to unwanted arthropods, meaning that their presence in the air, on the surface of an article, on the surface of a plant, or on the surface of a vertebrate, such as a human subject or other mammal, preferably a human subject, is undesirable. Preferably, the unwanted arthropods are harmful arthropods that affect plants and animals, such as thrips, aphids, beetles, moths, mealybugs, scale insects, etc., more preferably harmful arthropods that affect animals, such as ants, termites, cockroaches, flies, etc., even more preferably blood-sucking arthropods that affect vertebrates, such as biting flies, bedbugs, assassin bugs, fleas, lice, mosquitoes and ticks, even more preferably mosquitoes and ticks.

[0106] The presence of arthropods may be undesirable because their presence in the air is unpleasant to the subject, contact of arthropods with items may transfer disease and / or pathogens, or arthropods may bite organisms causing itching and transmission of disease and / or pathogens, or arthropod feeding may be the cause of other diseases and / or conditions.

[0107] In certain embodiments, the arthropod is an insect or an arachnid, preferably an insect.

[0108] The term "insect" has its normal understanding in the art by those skilled in the art. Insects are described by a distinct head, thorax, and abdomen, only three pairs of legs, and typically one or two pairs of wings.

[0109] In certain embodiments, the insect is a mosquito, biting fly, bed bug, assassin bug, flea, lice, ant, termite, cockroach, fly, aphid, beetle, thrips, moth, mealybug or scale insect, more preferably a mosquito.

[0110] The term "arachnid" has the usual understanding in the art by those skilled in the art and describes an arachnid that has a segmented body divided into two regions, the front of which has four pairs of legs but no antennae.

[0111] In certain embodiments, the arachnid is a tick, mite, chigger or spider, more preferably a tick.

[0112] Expressions such as "control", "arthropod control", "insect control" or "arachnid control" have their ordinary meaning to those skilled in the art.

[0113] "Control" in the context of the present invention defines the ability of an arthropod control composition according to the present invention to attract, deter, kill or repel arthropods, preferably to deter or repel arthropods, and even more preferably to repel arthropods.

[0114] "Attraction" according to the present invention defines the ability of an arthropod attractant composition according to the present invention to increase or promote the contact or presence of arthropods at an arthropod attractant source, for example, in the air, on the surface of an article, or on the surface of a vertebrate, for example, a human subject or other mammal, preferably on the surface of an article to which the arthropod attractant compound or composition has been applied, such as a trapping device.

[0115] "Repellent" according to the present invention defines the ability of an arthropod repellent composition according to the present invention to minimize, reduce, deter or prevent the approach or presence of arthropods at an arthropod repellent source, for example, in the air, on the surface of an item, or on the surface of a vertebrate, for example, a human subject or other mammal, preferably on the surface of a human subject to which the arthropod repellent compound or composition has been applied.

[0116] "Deterrence" according to the present invention defines the ability of an arthropod deterrent composition according to the present invention to minimize, reduce, prevent, or prevent the contact or presence of arthropods at an arthropod deterrent source, for example, in the air, on the surface of an item, or on the surface of a vertebrate, such as a human subject or other mammal, preferably on the surface of a human subject to which the arthropod deterrent compound or composition has been applied. Typically, deterrence is demonstrated when used as a bait-type deterrent that prevents subsequent feeding or egg-laying or physical contact by pests after initial ingestion of the arthropod deterrent compound or composition.

[0117] " Spatial repellency " according to the present invention defines the ability of the arthropod repellent composition according to the present invention to minimize, reduce, prevent or prevent the approach or presence of arthropods at the arthropod repellent source, for example, in the air, on the surface of an item, or on the surface of a vertebrate, such as a human subject or other mammal, preferably on the surface of a human subject to which the arthropod repellent compound or composition is applied.Typically, the spatial repellency effect is shown when the spatial repellent compound or composition is released, sprayed, scattered or diffused in the air or liquid, and prevents pests from entering the area where the spatial repellent compound or composition is present.Therefore, repellency occurs from a distance, and pests do not need to directly contact the treated item or organism to be protected.

[0118] "Killing" according to the present invention defines the ability of an arthropod-killing composition according to the present invention to kill arthropods at the source of arthropod killing, e.g., in the air, on the surface of an item, or on the surface of a vertebrate, e.g., a human subject or other mammal, preferably on the surface of a human subject to which the arthropod-killing compound or composition has been applied. When the arthropod-killing composition is applied to a plant, animal, or human subject, it is applied in an amount that kills the arthropods but does not kill the subject.

[0119] In certain embodiments, the pest arthropod control composition is an unwanted crawling arthropod or an unwanted flying arthropod control composition, preferably a control composition for any organism harmful to humans or human concerns, more preferably a blood-sucking arthropod control composition or a fiber-attacking arthropod or a stored-goods-attacking arthropod control composition, more preferably a cockroach or an ant or a termite or a bedbug or a tick or a mite or a flea or a ground beetle or a fly or a mosquito or a wasp or a hornet or a midge or a moth or a silverfish or a livestock parasitic fly or a fruit fly or a phorid fly or a stable fly or a louse or an assassin bug or a midge or a moth or a beetle control composition.

[0120] In certain embodiments, the arthropod control composition is a blood-sucking arthropod control composition, preferably an Aedes species or an Anopheles species or a Culex species or a Simulium species or an Ixodes species or a Rhipicephalus species or an Amblyomma species or an Argas species or an Ornithoideus species. hodoros species or Neotrombicula species or Phtirus species or Glossina species or Tabanus species or Atylus species or Chrysops species or Haematopota species or Haematobia species or Haematobosca species or Sa Stomoxys species or Phlebotomus species or Culicoides species or Ctenocephalides species or Phtirus species or Pediculus species or Triatoma species or Rhodnius species or Cimex species or Ixodes species or Koita The composition is a control composition for Rhipicephalus species, Amblyomma species, Argas species, Ornithodoros species, Neotrombicula species, Varroa species, Dermatophagoides species, Musca species, or Drosophila species.

[0121] In certain embodiments, the arthropod control composition is an arthropod control composition, preferably an insect control composition, more preferably a dipteran control composition.

[0122] In certain embodiments, the arthropod control composition is an Aedes species control composition, preferably an Aedes aegypti or Ae. albopictus control composition.

[0123] In another specific embodiment, the arthropod control composition is an Anopheles species control composition, preferably an An. gambiae or An. stephensis or An. quadrimatilacus or An. falauati control composition. Even more particularly, the arthropod control composition is an An. gambiae control composition.

[0124] In another specific embodiment, the arthropod control composition is a Culex species control composition, preferably a C. pipiens or C. quinquefasciatus or C. modestus or C. pinaresis or C. tritaeniorhynchus or C. sitiens or C. annulirostris control composition.

[0125] In another particular embodiment, the arthropod control composition is a fly control composition, preferably a leafminer or fruit fly or gall midge or spiral worm or botflies or black flies or house flies or stable flies or blow flies or tachinids or midges or sand flies, and more preferably a Drosophila suzuki or Drosophila melanogaster or Bactrocera dorsalis or Olive fruit fly (Ba. oleae) or Queensland fruit fly (Ba. tryoni) or Euleia heraclei or Anastrepha grandis grandis or Mexican fruit fly (An. ludens) or Western Indian fruit fly (An. obliqua) or Caribbean fruit fly (An. suspensa) or Strauzia longipennis or Rhagoletis mendax or Mediterranean fruit fly (Ceratitis capitata) or Ceratitis cosyra or Natal fruit fly (Ce. rosa) control composition.

[0126] In another specific embodiment, the arthropod control composition is a Simuliidae control composition, preferably a Simulium damnosum or Si. naevi or Si. callidum or Si. metallicum or Si. ochraceum or Si. ornatum or Si. posticatum or Si. variegatum or Si. bezzi or Si. erythrocephalum control composition.

[0127] In another particular embodiment, the arthropod control composition is a Glossina species control composition, preferably Gl. austeni or Gl. longipalpis or Gl. morsitans or Gl. pallidipes or Gl. swynnertoni or Gl. brevipalpis or Gl. fusca fusca) or Glossina fuscipleuris (Gl. fuscipleuris) or Glossina frezili (Gl. frezili) or Glossina haningtoni (Gl. haningtoni) or Glossina longipennis (Gl. longipennis) or Glossina medicorum (Gl. medicorum) or Glossina nashi (Gl. nashi) or Glossina nigrofusca (Gl. nigrofusca) or Glossina severini (G l.severini) or Glossina schwetzi or Glossina tabaniformis or Glossina vanhoofi or Glossina caliginea or Glossina fuscipes or Glossina pallicera or Glossina palpalis or Glossina tachinoides.In another specific embodiment, the arthropod control composition is a Tabanus species or Atylus species or Chrysops species or Haematopota species control composition, preferably Tabanus bovinus or Ta. autumnalis or Ta. bromius or Ta. eggeri or Ta. glaucopis or Ta. sudeticus or Chrysops relictus or Haematopota crassicornis control composition.

[0128] In another specific embodiment, the arthropod control composition is a Muscidae control composition, preferably a Haematobia species or a Haematobosca species or a Stomoxys species or a Drosophila species or a Musca species control composition, more preferably a Haematobia exigua or a Stomoxys calcitrans or a Musca domestica control composition.

[0129] In another specific embodiment, the arthropod control composition is a sand fly control composition, preferably a Phlebotomus ariasi or Phlebotomus balanicus or Phlebotomus intermedius or Phlebotomus longicuspis or Phlebotomus papatasi or Phlebotomus perniciosus or Phlebotomus sergenti control composition.

[0130] In another specific embodiment, the arthropod control composition is a Ceratopogonidae control composition, preferably a Culicoides occidentalis or Culicoides sanguisuga or Culicoides furens or Culicoides impunctatus control composition.

[0131] In another specific embodiment, the arthropod control composition is a flea control composition, preferably a cat flea (Ctenocephalides felis) or dog flea (Ct. canis) or human flea (Pulex irritans) or Archeopsylla erinace control composition.

[0132] In another specific embodiment, the arthropod control composition is a lice control composition, preferably a Phtirus pubis or Ph inguinalis or Pediculus humanus capitis or Pediculus humanus corporis or Liposcelis corroden or Li. decolor or Dorypteryx domestica control composition.

[0133] In another particular embodiment, the arthropod control composition is a Heteroptera control composition, preferably a Triatoma bug or bed bug control composition, more preferably Triatoma infestans or Triatoma barberi or Triatoma dimidiata or Triatoma nigromaculata or Triatoma protracta or Rhodnius prolixus or Panstrongylus geniculatus or Cimex lectularius The composition is a control composition for Simex lectularius, Simex hemipterus, Simex dissimilis, or Simex marginatus.

[0134] In another particular embodiment, the arthropod control composition is a beetle control composition, preferably an insect control composition selected from the group consisting of Acanthoscelides obtectus, Alphitobius diaperinus, Anobium punctatum, Anthrenus flavipes, An. munroi, An. museorum, An. pimpinellae, An. scrophulariae, An. verbasci, Attagenus unicolor, and Callosobruchus spp. maculatus) or Cryptolestes ferrugineus) or Cryptolestes busillus) or Dermestes lardarius) or European house longhorn beetle (Hylotrupes bajulus) or Lasioderma serricorne) or Lyctus brunneus) or Oryzaephilus surinamensis) or Rhyzopertha dominica) or Sitophilus granarius) or Si. oryzae) or Si. zeamais) or Stegobium paniceum) or Tenebrio moth molitor) or red flour beetle (Tenebroides mauritanicus) or red flour beetle (Tribolium castaneum) or flat-headed red flour beetle (Tr.confusum) or small red flour beetle (Trogoderma granarium) or small spotted flour beetle (Tr.inclusum) or black spotted flour beetle (Tr.It is a composition for controlling Tr. longisetosum or Tr. variabilekissing.

[0135] In another specific embodiment, the arthropod control composition is a moth control composition, preferably a Cadra cautella or Corcyra cephalonica or Endrosis sarcitella or Ephestia elutella or Ep. kuehniella or Hofmannophila pseudospretella or Nemapogon granella or Indian meal moth or Plodia interpunctella or Pyralis farinalis or Sitotroga cerealella control composition.

[0136] In another specific embodiment, the arthropod control composition is a cockroach control composition, preferably a Blatta species or a Blattella species or a Periplaneta species control composition, more preferably a Blatta orientalis or a Blatella germanica or a Periplaneta americana control composition. In another specific embodiment, the arthropod control composition is an ant control composition, preferably a Lasius species or a Solenopsis species or a Myrmica species control composition, more preferably a Monomorium pharaonis ant or a Lasius niger ant or a Solenopsis invicta ant or a Myrmica rubra ant or an Argentine ant or a Linepithema humile ant or a Tapinoma melanocephalum ant or a Lasius neglectus ant or a Tapinoma erraticum control composition.

[0137] In certain embodiments, the arthropod control composition is an arachnid control composition, more preferably a tick control composition.

[0138] In another specific embodiment, the arthropod control composition is an Ixodes species control composition, preferably an Ixodes ricinus tick or an I. scapularis tick or an I. persulcatus tick or an I. pacificus tick or an I. holocyclus tick or an I. ovatus tick or an I. uriae tick or an I. hexagonus tick or an I. acuminatus tick.

[0139] In another specific embodiment, the arthropod control composition is a Rhipicephalus species control composition, preferably an R. sanguineus or R. haemaphysaloides or R. phoenix control composition.

[0140] In another specific embodiment, the arthropod control composition is an Amblyomma species control composition, preferably an Amblyomma variegatum or an Amblyomma americanum or an Am. testudinarium control composition.

[0141] In another specific embodiment, the arthropod control composition is an Argasidae control composition, preferably an Argas monolakensis or Ar. persicus or Ar. reflexus or Ornithodoros coriaceus or Ornithodoros erraticus or Ornithodoros concanensis control composition.

[0142] In another particular embodiment, the arthropod control composition is a mite control composition, preferably selected from the group consisting of Neotrombicula autumnalis, Varroa destructor, V. jacobsoni, V. rindereri, Varroa sinhai, Sarcoptes scabiei, Sarcoptes species, Dermatophagoides pteronyssinus, Dermanyssus gallinae, Ornithonyssus sylviarum, Acarus siro, Lepidoglyphus destructor, and Tyrophagus The composition is a composition for controlling Tyrophagus longior or Tyrophagus putrescentiae.

[0143] In certain embodiments, the arthropod control composition is an agricultural pest control composition, preferably an insect or acarine or nematode control composition.

[0144] In certain embodiments, the arthropod control source is the surface and / or air near an article, preferably a candle, coil, powered diffuser, wristband, patch, collar, ear tag, clothing, fabric, paper, biochar, cardboard, cellulose pad, mosquito net, screen, curtain, furniture, wall, primer or paint, or the surface of a subject, preferably a vertebrate, such as a human subject or other mammal, preferably a human subject, i.e., the skin of a human subject treated with a product such as a spray, aerosol, cream, roll-on, wristband, lotion, soap, shampoo, sunscreen or patch, or fabric treated with a product such as laundry powder, liquid detergent, spray, lotion, powder, etc.

[0145] Arthropod control efficacy can be determined against mosquitoes using an adapted warm body assay as defined in Krober T, Kessler S, Frei J, Bourquin M, Guerin PM. An in vitro assay for testing mosquito controlling compounds employing a warm body and carbon dioxide as a behavioral activator. J Am Mosq Control Assoc. 2010;26:381-386.

[0146] Control efficacy, repellency, and spatial repellency can be determined by testing the warm body assay against the yellow fever mosquito, Aedes aegypti, Rockefeller strain. A. aegypti is a highly aggressive human parasitic mosquito species that generally exhibits low susceptibility to arthropod control compounds, making it a model organism for control testing and one of the model organisms recommended by the World Health Organization (WHO). Observations of control efficacy are performed on host-seeking females of uniform age, 5–10 days old, selected as described in the publications mentioned above. Tested fasting females have access to a 10% sugar solution but are not given blood.

[0147] Control efficacy, repellency, and spatial repellency can also be determined according to the arm-in-the-box method, adapted from the WHO guidelines for testing the efficacy of mosquito repellents on human skin (WHO / CDS / NTD / WHOPES / 2009.4). The readiness of 100 hungry female A. aegypti mosquitoes to the test substance is assessed by inserting them into a cage (40 x 40 x 40 cm) three times for 30 seconds (negative control) and comparing the results of the untreated arm with those of the treated arm.

[0148] The activity of substances to repel ticks and other arachnids was evaluated using the in vitro worm plate assay protocol defined in Krober T, Bourquin M, Guerin PM. 2013. A standardized in vivo and in vitro test method for evaluating tick repellents. Pestic. Biochem. Phys. 107(2):160-168.

[0149] In certain embodiments, the compositions of the present invention comprise an arthropod-controlling effective amount of the compound.

[0150] In certain embodiments, the composition comprises the compound in an amount of 0.00032 to 30% by weight, preferably 0.001 to 10% by weight, more preferably 0.5 to 5% by weight, based on the total weight of the composition.

[0151] In certain embodiments, the composition comprises the compound in an amount of 0.00032 to 20% by weight, preferably 0.001 to 10% by weight, based on the total weight of the composition.

[0152] In certain embodiments, the composition comprises the compound in an amount of 0.001 to 1% by weight, based on the total weight of the composition.

[0153] In certain embodiments, the composition comprises the compound in an amount of 0.01 to 1% by weight, preferably 0.5 to 1% by weight, based on the total weight of the composition.

[0154] In certain embodiments, the composition comprises the compound in an amount of at least 0.01% by weight, based on the total weight of the composition.

[0155] In certain embodiments, the composition comprises the compound in an amount of at least 0.04% by weight, based on the total weight of the composition.

[0156] In certain embodiments, the composition is preferably liquid at room temperature (25°C) and comprises the compound in an amount of 0.001 mg / mL to 100 mg / mL, preferably 0.001 mg / mL to 10 mg / mL, more preferably 0.016 mg / mL to 10 mg / mL, even more preferably 0.08 mg / mL to 10 mg / mL, and most preferably 0.4 mg / mL to 10 mg / mL.

[0157] In certain embodiments, the amount and selection of agents is in a manner that contributes to, enhances, or improves both the arthropod control activity and the hedonic properties of the composition.

[0158] In certain embodiments, the arthropod control composition may further comprise an arthropod control co-ingredient. By "arthropod control co-ingredient" is understood an ingredient that can provide an arthropod control benefit in addition to the arthropod control effect of the compositions described herein.

[0159] In certain embodiments, the described compounds can modify, enhance, or improve the arthropod control efficacy of an arthropod control co-ingredient, for example, by reducing the amount of the arthropod control co-ingredient in the composition, which can be particularly beneficial when the arthropod control co-ingredient is harmful to human subjects at certain doses or when the arthropod control co-ingredient has unpleasant olfactory properties at certain doses.

[0160] According to certain embodiments, the combination of a compound described herein with an arthropod control co-ingredient provides a synergistic arthropod control effect.

[0161] According to certain embodiments, the combination of a material described herein with an arthropod control co-ingredient results in an altered, pleasant, enhanced, or improved olfactory impression of the overall composition compared to the component alone.

[0162] According to certain embodiments, the arthropod control co-ingredient may be selected from the group consisting of N,N-diethyl-3-methylbenzamide (DEET), ethyl butylacetylaminopropionate (IR3535); paramenthan-3,8-diol (PMD); 1-(1-methylpropoxycarbonyl)-2-(2-hydroxyethyl)piperidine (picaridin); Chinese cedarwood oil, Texas cedarwood oil, Virginia cedarwood oil, cinnamon oil, citronella oil, corn mint oil, Java citronella (Cymbopogon winterianus) oil fractionated hydrated cyclized oil, decanoic acid, Eucalyptus citriodora oil, Eucalyptus citriodora oil hydrated cyclized oil, eugenol, garlic oil, geraniol, geranium oil, lavender oil, Lavandula hybrida (Lavandula angustifolia) oil, and the like. hybrida) oil, lavandin oil, lemon oil, lemongrass oil, neem extract, metofluthrin, cis- and trans-p-menthane-3,8-diol mixture, N,N-diethyl-meta-toluamide, nonanoic acid, rosemary oil, thyme oil, wintergreen oil, 2,3,4,5-bis(butyl-2-ene)tetrahydrofurfural (MGK Repellent 11), cineole, cinnamaldehyde, citronellal, citronellol, coumarin, dibutyl phthalate, diethyl phthalate, dimethyl anthranilate, dimethyl phthalate, ethyl vanillin, eucalyptus oil, hydroxycitronellal, lime oil, limonene, linalool, methyl anthranilate, mint oil, myrcene, neem oil, sabinene, β-caryophyllene, (1H-indol-2-yl)acetic acid, anethole, anise oil, basil oil, bay leaf oil, camphor, ethyl salicylate, evergreen oil (pine oil), clove oil, nootkatone, 2-undecanone, sulcatone, (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)methyl 2,2-Dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate (d-tetramethrin), 3-allyl-2-methyl-4-oxocyclopent-2-enyl-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate (d-allethrin), α-cyano-3-phenoxybenzyl, 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecal Boxilate (cypermethrin), 2-methyl-4-oxo-3-(prop-2-ynyl)cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate (prallethrin), acetamiprid, azadirachtin, bendiocarb, bifenthrin, boric acid, chlorpyrifos, deltamethrin, diazinon, dichlorovos, eugenol, fipronil , imidacloprid, malathion, maltodextrin, metofluthrin, nicotine, permethrin, pyrethrins, pyrethroids, rotenone, silicon dioxide (diatomaceous earth), S-methoprene, spinosad (spinosyn A), spinosyn D, tetramethrin, transfluthrin, 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one, 3-butylidene-2-benzofuran -1-one, 4-ethenyl-2-methoxyphenol, Cognac Green Oil, Labdanum Extract (Cistus Species), 5-Pentylxolan-2-one, Chromen-2-one, 3,7-Dimethylocta-2,6-dienal, 4-Hydroxy-3-methoxybenzaldehyde, 2-Methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one, Spearmint (Mentha spicata) Oil, 6-Hexyloxan-2-one, 5-Methyl-2-propan-2-ylcyclohexyl]acetate, Nigella damascena Oil, 2-Phenylethanol, 6-Pentyloxan-2-one, (4-Methoxyphenyl)methyl Acetate, Clove (Syzygium aromaticum) Oil, 3,4,4a,5,6,7,8,8a-Octahydrochromen-2-one, 3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene, 2-phenylethyl 2-methylpropanoate, methyl 2-(3-oxo-2-pent-2-enylcyclopentyl)acetate, 4-(2-methoxypropan-2-yl)-1-methylcyclohexene, peppermint (Mentha piperita) oil, 2-methoxy-4-[prop-1-enyl]phenol, 2-methyl-3-(4-propan-2-ylphenyl)propanal, (4-methoxyphenyl)methanol, 2,3-dihydro-1H-indene-2-carbonitrile, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2,5-di Methyl-2,3-dihydro-1H-inden-2-yl)methanol, (4aRS,9bRS)-4a,7-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2RS,4aRS,9bRS)-2,4a,7-trimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2RS,4aSR,9bSR)-2,4a,7-trimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][ 1,3]dioxin, (2-methyl-1,3-dihydroinden-2-yl)methanol, 2,3-dihydro-1H-inden-2-ylmethanol, (2RS,4RS,4ASR,9BRS)-2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2RS,4aRS,9bSR)-2-methyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2RS,4aSR,9bRS)-2-methyl -4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (4aRS,9bSR)-2,2-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2,4,6-trimethyl-2,3-dihydro-1H-inden-2-yl)methanol, 5-(tert-butyl)1,3-dihydrospiro[indene-2,3'-oxetane], (2RS,4RS,4ARS,9BSR)-2,4-dimethyl-4,4a,5,9b-Tetrahydroindeno[1,2-d][1,3]dioxine, 4a,8-dimethyl-indano[1,2-d]-1,3-dioxan-2-one, 1-(2,5-dimethyl-2,3-dihydro-1H-inden-2-yl)ethanone, (5-methyl-2,3-dihydro-1H-inden-2-yl)methanol, (4aRS,9bSR)-8-methyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2R S,4aRS,9bSR)-2-ethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2RS,4aSR,9bRS)-2-ethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2R,4aS,9bS)-2,4a,8-trimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, 1-(2,5-dimethyl-2-indanyl)- 1-Ethanol, (2,5-dimethyl-2,3-dihydro-1H-inden-2-yl)methanol, (2RS,4aRS,9bSR)-2,8-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2RS,4aSR,9bRS)-2,8-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2RS,4aSR,9bSR)-2,4a-dimethyl-4,4a ,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (4aRS,9bRS)-4a,8-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, 1-(2,4,5-trimethyl-2,3-dihydro-1H-inden-2-yl)ethenone, (2RS,4aRS,9bSR)-2-ethyl-8-methyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2RS,4aSR,9bRS)-2-ethyl-8-methyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (4aRS,9bRS)-2,2,4a,8-tetramethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, 5-tert-butyl-indan-2-spiro-3'-oxetane, (2,6-dimethyl-1,2,3,4-tetrahydro-2-naphthalenyl)methanol, (4aRS,9bRS)-2,2,4a-trimethyl-4,4a,5,9b-tetrahydroindeno[1 ,2-d][1,3]dioxin, (4aRS,9bRS)-2,2,4a,7-tetramethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, 3-(3 / 4-ethylcyclopent-1-en-1-yl)-2-methylpropanal, 3-(3 / 4-propylcyclopent-1-en-1-yl)-2-methylpropanal, 3-(3 / 4-butylcyclopent-1-en-1-yl)-2-methylpropanal, 3-(3 / 4-isopropylcyclopent-1-en-1-yl)-2-methylpropanal, 3-(3 / 4-(sec-butyl)cyclopent-1-en-1-yl)-2-methylpropanal, 3-(3 / 4-(tert-butyl)cyclopent-1-en-1-yl)-2-methylpropanal, 3-[4-(2-methoxy-2-propanyl)-2-methylphenyl]propanal, 3-[4-(2-hydroxy-2-methylpropyl)phenyl]propanal, 3-(4-tert-butyl-2-methylphenyl)propanal, 3-(4-tert-butylphenyl)propanal, 3-(3-propan-2-ylphenyl)butanal, 3-(4- 2,6-Dimethoxy-4-[prop-1-enyl]phenol, 4-allyl-2,6-dimethoxyphenol, 1,2,3-trimethoxy-5-[1-propen-1-yl]benzene, 1,2,3-trimethoxy-5-propylbenzene, 1,2,4-trimethoxybenzene, 2,6-dimethoxy-4-propylphenol, 2,6-dimethoxy-4-methylphenol, 3-(3,4,5-trimethoxyphenyl)propen-2-oic acid, 2-(4-hydroxy-3-methoxyphenyl)acetic acid, methyl 3-(3,4-Dimethoxyphenyl)-2-methylpropanoate, (2,3-dimethoxyphenyl)methanol, 2,3,4-trimethoxybenzaldehyde, 3,4,5-trimethoxybenzaldehyde, 2-ethoxy-4-(methoxymethyl)phenol, 2-ethoxy-4-(ethoxymethyl)phenol, 1,2-dimethoxy-4-prop-1-enylbenzene, 1,2,3-trimethoxy-5-methylbenzene, 2,6-dimethoxy-4-methylphenol, 1-(2,3,4-trimethoxyphenyl)ethanone, 7-methyl-1,5-benzodioxepin-3-one, 1,2-dimethoxy-3-prop-1- The compound is selected from the group consisting of phenylbenzene, 1,2,3-trimethoxy-5-propylbenzene, 2,3,4-trimethoxybenzonitrile, 3-ethoxy-4-methoxybenzaldehyde, 2,3,4-trimethoxyphenol, 1-(4-hydroxy-3-methoxyphenyl)ethanone, 2-methoxy-4-(4-methylideneoxan-2-yl)phenol, 4-(3,6-dihydro-4-methyl-2H-pyran-2-yl)-2-methoxyphenol, 3-(4-isopropyl-2-methylphenyl)propanal, 3-(2-isopropyl-4-methylphenyl)propanal, and mixtures thereof.

[0163] In certain embodiments, the arthropod control co-ingredient is included in the composition in an amount of 0.02 to 80% by weight, more preferably 0.05 to 70% by weight, and even more preferably 0.1 to 60% by weight, based on the total weight of the composition, whereby the composition is understood to include an arthropod control co-ingredient in a minimum amount of at least 0.02%, at least 0.05%, or at least 0.1% by weight, and a maximum amount of 80% by weight or less, 70% by weight or less, or 60% by weight or less, based on the total weight of the composition.

[0164] In certain embodiments, the compound and arthropod control co-ingredient in the compositions of the present invention are present in the composition in a weight range of 90:10 to 10:90, preferably in a weight range of 80:20 to 20:80, more preferably in a weight range of 65:35 to 35:65, and most preferably in a weight range of 60:40 to 40:60. It is also understood herein that the compound and arthropod control co-ingredient can be present in the composition in any weight range combination described above, such as 90:10 to 20:80, preferably 35:65, more preferably 40:60, 80:20 to 10:90, preferably 35:65, more preferably 40:60, 65:35 to 10:90, preferably 20:80, more preferably 40:60, or 40:60 to 10:90, preferably 20:80, more preferably 35:65.

[0165] In one embodiment, the arthropod control composition may further comprise a fragrance component. It is understood that the fragrance component contributes to, modifies, enhances, or improves the olfactory properties of the composition, but does not contribute to, enhance, or improve the arthropod control effect of the composition. Fragrance components that provide such hedonic effects and are suitable for use in the compositions of the present invention are known in the art and can be easily identified by those skilled in the art.

[0166] The arthropod control composition may further comprise a carrier. A "carrier" is understood to be a material with which the active compound is mixed or formulated to facilitate its application to a site or other object to be treated, or its storage, transportation, and / or handling. The carrier may be of inorganic or organic or synthetic natural origin. The carrier may be liquid or solid.

[0167] As liquid carrier, non-limiting examples can include emulsifying system, that is, solvent system and surfactant system, or the solvent commonly used in cosmetics.The detailed description of the nature and type of solvent generally cannot be exhaustive.But non-limiting examples can include solvents such as butylene or propylene glycol, glycerol, dipropylene glycol and its monoether, 1,2,3-propanetriyl triacetate, dimethyl glutarate, dimethyl adipate 1,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1-ethanol, triethyl citrate, 2-methylprop-1-ene and 2-(2-ethoxyethoxy)ethanol or their mixtures, and particularly suitable are dipropylene glycol, 2-methylprop-1-ene and 2-(2-ethoxyethoxy)ethanol and their mixtures.

[0168] In the case of compositions comprising a carrier, suitable carriers other than those specified above may be ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar® (manufactured by Exxon Chemical), or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (manufactured by Dow Chemical Company), for example Dowanol™ DPMA (glycol ether acetate), or Augeo® Clean Multi (isopropylidene glycerol; manufactured by Solvay), or hydrogenated castor oil such as those known under the trademark Cremophor® RH40 (manufactured by BASF).

[0169] In certain embodiments, the composition further comprises ethanol, in certain embodiments, the composition comprises ethanol in an amount of 80 to 99.9 wt % based on the total weight of the composition.

[0170] The term "solid carrier" refers to a material to which the arthropod control composition or some components of the arthropod control composition can be chemically or physically bound. Generally, such solid carriers are used to stabilize the composition or to control the evaporation rate of the composition or some components. The use of solid carriers is currently used in the art, and those skilled in the art know how to achieve the desired effect. However, non-limiting examples of solid carriers include absorbent gums or polymers or inorganic materials, such as porous polymers, cyclodextrins, wood-based materials, organic or inorganic gels, clays, gypsum talc, or zeolites.

[0171] Other non-limiting examples of solid carriers can include encapsulating materials.Examples of such materials can include wall-forming and plasticizing materials such as monosaccharides, disaccharides or trisaccharides, natural or modified starch, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, protein or pectin, or other such materials.Encapsulation is a process well known to those skilled in the art, and can be carried out by using techniques such as spray drying, coagulation or even extrusion, or can consist of coating encapsulation, including coacervation and complex coacervation techniques.

[0172] Non-limiting examples of solid carriers include core-shell capsules with aminoplast, polyamide, polyester, polyurea or polyurethane type resins, or mixtures thereof (all of which are well known to those skilled in the art), using techniques such as phase separation processes induced by polymerization, interfacial polymerization, coacervation or all of which are described in the prior art, optionally in the presence of polymeric stabilizers or cationic copolymers.

[0173] Resins can be produced by polycondensation of aldehydes (e.g., formaldehyde, 2,2-dimethoxyethanal, glyoxal, glyoxylic acid, or glycolaldehyde, and mixtures thereof) with amines such as urea, benzoguanamine, glycoluril, melamine, methylolmelamine, methylated methylolmelamine, guanazole, and mixtures thereof. Alternatively, preformed resins, such as alkylolated polyamines, can be used, such as those commercially available under the trademarks Urac® (manufactured by Cytec Technology Corp.), Cymel® (manufactured by Cytec Technology Corp.), Urecoll®, or Luracoll® (manufactured by BASF).

[0174] Other resins are produced by polycondensation of polyols such as glycerol and polyisocyanates, such as the trimer of hexamethylene diisocyanate, the trimer of isophorone diisocyanate or xylylene diisocyanate, or the biuret of hexamethylene diisocyanate, or the trimer of xylylene diisocyanate with trimethylolpropane (known under the trade name Takenate®, manufacturer: Mitsui Chemicals, Inc.), among others the trimer of xylylene diisocyanate with trimethylolpropane and the biuret of hexamethylene diisocyanate.

[0175] In certain embodiments, the composition does not include acetyl cedrene.

[0176] In certain embodiments, the composition comprises (9E)-9-ethylidene-3-oxatricyclo[6.2.1.0 2,7 ]Undecane-4-one is not included.

[0177] In certain embodiments, the composition does not include nepetalactone.

[0178] The present invention also relates to a method for controlling arthropods, preferably insects, which comprises directly contacting or contacting the arthropods, preferably insects, with the vapor of a composition according to the invention.

[0179] For clarity, arthropod control compositions according to the present invention can be applied to the air, the surface of an article, the air near the surface of an article, or the surface of interest by conventional methods known in the art, such as spraying, painting, attaching, or spreading.

[0180] In certain embodiments, arthropod control compositions according to the present invention are applied to the surface of an article, to the air near the surface of an article, or to the surface of an animal or subject.

[0181] In certain embodiments, the article may be an arthropod control article as described below, and may be a candle, a coil, a powered diffuser, a wristband, a patch, a collar, an ear tag, clothing, fabric, paper, biochar, cardboard, cellulose pad, mosquito net, a screen, a curtain, furniture, paint, a wall, a primer, a spray, an aerosol, a cream, a roll-on, a wristband, a lotion, a soap, a shampoo, a sunscreen, a laundry powder, a liquid detergent, a spray, a lotion, or a powder, among others.

[0182] In certain embodiments, the surface of the subject is the surface of a human or animal subject, preferably the surface is a human subject, i.e., the skin of a human subject.

[0183] The present invention also relates to the use of the compositions according to the invention for controlling arthropods, preferably insects.

[0184] The present invention also relates to consumer products comprising the compositions according to the invention.

[0185] Non-limiting examples of suitable consumer products include fragrances, such as finely divided fragrances, splashes or eau de parfum, colognes, or shaving or aftershave lotions, or creams or gels; fabric care products, such as liquid or solid detergents, fabric softeners, liquid or solid scent boosters, fabric refreshers, ironing water, paper, bleach, carpet cleaners, curtain care products; body care products, such as hair care products (e.g., shampoos, coloring preparations or hair sprays, color care products, hair shaping products, dental care products), disinfectants, intimate care products; cosmetic preparations (e.g., skin creams or lotions, vanishing creams, or deodorants or antiperspirants (e.g., sprays or roll-ons), depilatories, tanning products, tanning or after-sun products, nail products, skin cleansing, makeup); or skin care products (e.g., soaps, shower or bath mousses, oils or gels, or hygiene products, or foot / hand care products); air fresheners, and the like. Care products, for example deodorisers or "ready-to-use" powder deodorisers that can be used in domestic spaces (rooms, refrigerators, cupboards, shoes or cars) and / or public spaces (hall, hotel, mall, etc.); or home care products, for example mould removers, furniture care products, wipes, dishwashing detergents or detergents for hard surfaces (for example floor, bath, sanitary or window cleaning); leather care products; car care products, for example polishes, waxes or plastic cleaners; candles; sprays, coils, electric diffusers, piezoelectric diffusers, liquid motorized diffusers, diffusers, rubber septa, wristbands, patches, collars, ear tags, clothing, fabric, paper, biochar, cardboard, cellulose pads, mosquito nets, screens, curtains, varnish or paint, more preferably candles, sprays, coils, motorized diffusers, piezoelectric diffusers, liquid motorized diffusers, diffusers, rubber septa, wristbands, patches, collars, ear tags, clothing, fabric, paper, biochar, cardboard, cellulose pads, mosquito nets, screens, curtains, varnish or paint.

[0186] In a preferred embodiment of the present invention, the consumer product is a powered diffuser. In this embodiment of the present invention, the substance in the arthropod, preferably insect, control composition is present in a fixed amount.

[0187] The present invention is further illustrated by the following non-limiting examples.

[0188] Example 1. Experimental protocols and methods used 1.1 The Warm Body Assay is a small-scale test used to screen mosquito repellent efficacy at concentrations 3-15 at TO.

[0189] Aedes aegypti is a highly aggressive human parasitic mosquito species that generally exhibits low susceptibility to arthropod control compounds, making it a model organism for control testing and one of the model organisms recommended by the World Health Organization (WHO). Anopheles gambiae is also a model organism because it is a human parasite and transmits malaria.

[0190] The control efficacy of the present invention was evaluated using an adapted warm body assay as defined in Krober T, Kessler S, Frei J, Bourquin M, Guerin PM. 2010. J Am Mosq Control Assoc. 26:381-386. In this in vitro assay, the number of mosquitoes landing on a warm body mimicking an attractive host treated with a test stimulus was measured to assess repellency.

[0191] The published protocol was adapted by switching from Anopheles gambiae to Ae. aegypti, resulting in a reduction in the number of mosquitoes placed in the test cages due to size differences (i.e., 30 mosquitoes instead of 50), and an increase in illumination (i.e., 150 lux instead of 4 lux) because Ae. aegypti is a diurnal mosquito.

[0192] Sandblasted glass petri dish (28.3cm) covering the worm body 2 100 μL of compounds diluted to different concentrations in ethanol were applied to the warm bodies. For each stimulus, the number of mosquitoes landing on the warm bodies was counted. Data were normalized using the number of landings in the pure ethanol (solvent) control treatment, and the percentage of repellency was calculated.

[0193] 1.2 The Arm-in-Cage test is a large-scale test used to evaluate mosquito repellent efficacy over time in human volunteers.

[0194] The arm-in-the-box method was adapted from the WHO guidelines for testing the efficacy of mosquito repellents on human skin (WHO / CDS / NTD / WHOPES / 2009.4) and / or based on the EU biocide testing guidelines (Guidance on the Biocidal Products Regulation. Vol. II Efficacy-Assessment and Evaluation (Parts B+C), v.4.0. December 2021). The search readiness of 200 hungry female mosquitoes, Aedes aegypti (Ae. aegypti) or 50 Anopheles gambiae (An. gambiae), was assessed by inserting the untreated arm of a human volunteer into a cage (40 × 40 × 40 cm) for 30 seconds to determine search activity (negative control). The product was then applied to the skin of the human volunteer's forearm (600 cm). 2After 5 minutes (Ae. aegypti) or 30 minutes (An. gambiae), the arm is inserted into the cage and exposed for 3 minutes. The assay is performed in a temperature (27 ± 2 °C) and humidity (80 ± 10% RH) controlled room on three different human volunteers.

[0195] 1.3 The Warm Plate Assay is a small-scale test used to screen the repellent efficacy against ticks at TO at different concentrations.

[0196] The repellent efficacy of different compounds was evaluated against the castor bean tick, Ixodes ricinus L., which is capable of transmitting both bacterial and viral pathogens. Ixodes ricinus is one of the recommended model organisms mentioned in the Guidance on the European Biological Products Regulation (Vol II, Efficacy-Assessment & Evaluation (Parts B+C), v3.0, April 2018). Repellent efficacy observations were performed on terminal nymph stages.

[0197] Repellent efficacy was evaluated using the in vitro worm plate assay protocol defined in Krober T, Bourquin M, Guerin PM. 2013. A standardized in vivo and in vitro test method for evaluating tick repellents. Pestic. Biochem. Phys. 107(2):160-168.

[0198] 2. Results of deterrent and spatial repellency effects on arthropods 2.1 Results of the warm body assay for mosquitoes: a small-scale assay to assess deterrence and spatial avoidance

[0199] As shown in Table 1 below and Figure 1, saturated γ-lactones with short hydrocarbon chains (fewer than 7 carbons) or long carbonyl chains (more than 10 carbons) were less effective at repelling Aedes aegypti mosquitoes (Ae. aegypti) than γ-lactones containing 7-10 carbons.

[0200] The results for three concentrations per stimulus are shown in Table 1. The R chain corresponds to the carbon chain attached to the oxolan-2-one at position 5. The mean number of mosquito landings in the solvent alone (0 mg / mL) was equal to 66.7 ± 7.7 times in 2 min.

[0201] [Table 3]

[0202] Table 1 shows that the unsaturated γ-lactones tested were more effective than their saturated counterparts, i.e., with the same carbon chain length, the presence of unsaturation conferred greater repellent potency to the compounds. This can also be observed from Figure 1, where the data from the table for the second concentration (0.4 mg / mL) is again shown.

[0203] The observations made in Table 1 and Figure 1, respectively, show that C across 13 different concentrations 10 This was confirmed by accurate measurements of γ-lactone repellency against Aedes aegypti (see Figure 2). 10 The repellent effect of the γ-lactone, 5-hex-3-enyloxolan-2-one, was observed in saturated C 10 This is significantly greater than the repellent effect of the γ-lactone, 5-hexyloxolan-2-one (paired t-test, p=0.026; see FIG. 2).

[0204] Similarly, both C 10Unsaturated γ-lactones showed a relevant dose-response repellent effect against An. gambiae, demonstrating a clear biological effect of the stimuli on the mosquitoes (see Table 2). Eight concentrations of each stimuli were evaluated. The average number of mosquito landings on the solvent alone (0 mg / mL) was equal to 50.0 ± 4.7 times in 2 minutes. As soon as the concentration of one of these unsaturated γ-lactones exceeded 0.09%, Anopheles mosquitoes refused to land on the attractive worm bodies, demonstrating a strong repellent effect (see Table 2).

[0205] [Table 4]

[0206] Similar to γ-lactones, unsaturated δ-lactones were also found to be more efficient at repelling Aedes aegypti mosquitoes (Ae. aegypti) than their saturated counterparts, with lower doses of unsaturated δ-lactones being sufficient to reach similar efficacy (see Table 3). In particular, the unsaturated C 10 The δ-lactones 6-pent-2-enyloxan-2-one and 6-pent-3-enyloxan-2-one are saturated C 10 It was significantly more effective at repelling mosquitoes than the δ-lactone 6-pentyloxan-2-one (paired t-test, p=0.01 and p=0.04, respectively; see Table 3 and Figure 3). Among C7 δ-lactones, the unsaturated 6-ethenyloxan-2-one, when applied at a concentration of 10 mg / mL (applied at an absolute concentration of 1 mg), prevented any mosquitoes from landing, whereas when the same amount of its saturated counterpart, 6-ethyloxan-2-one, was applied, more than 50% still landed (see Table 3). 11 For δ-lactones, protection is provided by the saturated C 11 It was higher at both 0.4 mg / mL and 10 mg / mL concentrations compared to the δ-lactone (see Table 3).

[0207] [Table 5]

[0208] Similar results were obtained with An. gambiae, where unsaturated δ-lactones, like γ-lactones, were more efficient than their saturated counterparts at repelling these mosquitoes. As proof of concept, unsaturated C 10 The δ-lactones 6-pent-2-enyloxan-2-one and 6-pent-3-enyloxan-2-one are saturated C 10 It was significantly more effective at repelling mosquitoes than the δ-lactone 6-pentyloxan-2-one (paired t-test, p=0.001 and p=0.007, respectively; see Figure 4). Indeed, as with Aedes aegypti, lower doses were required to reach similar efficacy.

[0209] Additionally, three β-lactones and five ε-lactones were also screened for repellent effects against Aedes aegypti (Ae. aegypti) (see Table 4).

[0210] [Table 6]

[0211] Similar to δ- and γ-lactones, unsaturated β- and ε-lactones provided a faster repellent effect compared to saturated β- and ε-lactones (see Table 4). For example, the β-lactone 3-buta-1,3-dienyl-4-pentyloxetan-2-one already repelled over 80% of mosquitoes at a concentration of 0.4 mg / mL, whereas at this same concentration, 3,3-dimethyl-4-propan-2-yloxetan-2-one repelled less than 40% (see Table 4). Similarly, unsaturated ε-lactones showed a C of 0.4 mg / mL. 11As highlighted by the results with ε-lactones, the unsaturated 7-pent-4-enyloxepan-2-one provided better repellency, already reaching 95% repellency, while its saturated counterpart 7-pentyloxepan-2-one only reached 52% (see Table 4).

[0212] More complex lactones were also further screened for repellent effects against Aedes aegypti (see Table 5), and all of them showed greater than 50% repellency at a concentration of 0.4 mg / mL (see Table 5).

[0213] [Table 7]

[0214] Mixing unsaturated lactones together or with other compounds was also able to induce relevant repellency against Aedes aegypti mosquitoes (see Table 6).

[0215] [Table 8]

[0216] 2.2 Mosquito arm-in-cage assay results: a large-scale assay to assess deterrence and spatial avoidance

[0217] Based on the arm-in-cage test, the repellency persistence of different compounds can be evaluated.

[0218] A 20% solution of 5-hex-3-enyloxolan-2-one diluted in ethanol was found to induce greater than 90% mosquito protection for Ae. aegypti for 2 hours and An. gambiae for 5 hours (see Table 7). 10When tested against An. gambiae, gamma-lactone even provided 100% protection during 4 hours, ie no mosquitoes landed (see Table 7).

[0219] On the untreated arm, 416 mosquitoes landed in the Ae. aegypti experiment and 40 mosquitoes landed in the An. gambiae experiment during the 3-minute test period. For human volunteers, the test was stopped when the repellency rate fell below 90%. nd is indicated when no measurements were taken.

[0220] [Table 9]

[0221] As already observed in the warm body assay, unsaturated C 10 The δ-lactones 6-pent-2-enyloxan-2-one and 6-pent-3-enyloxan-2-one exhibited saturated C 10 It repelled Aedes aegypti more effectively than the δ-lactone 6-pentyloxan-2-one (paired t-test, p=0.04 and p=0.05, respectively; see FIG. 5).

[0222] Δ-lactones were also found to be effective in repelling An. gambiae, with 6-pent-2-enyloxan-2-one and 6-pent-3-enyloxan-2-one providing greater than 90% repellency for 6 and 8 hours, respectively (see Table 8). Diluting these compounds to 20% with ethanol even provided 100% protection against An. gambiae, i.e., no mosquitoes landed, for 4 and 3 hours, respectively (see Table 8).

[0223] Even at a 5% dilution, 6-pent-2-enyloxan-2-one showed repellency against An. gambiae of 100% ± 0%, 99.2% ± 1.3%, and 67.2% ± 7.9% at 30 minutes, 1 hour, and 2 hours after application, respectively.

[0224] In Table 8, each time point represents the mean ± SD of the percentage of repellency compared to the untreated arm for three different human volunteers. During the 3-minute test period for the 6-pent-2-enyloxan-2-one and 6-pent-3-enyloxan-2-one experiments, 56 and 40 mosquitoes were released onto the untreated arm, respectively. For human volunteers, the test was stopped when the repellency rate fell below 90%, and the values ​​shown are indicative of the mean repellency.

[0225] [Table 10]

[0226] As shown in Table 9, 3,6-dimethyl-3a,4,5,6,7,7a-hexahydro-3H-1-benzofuran-2-one repelled over 95% of both species of mosquitoes for at least 1 hour.

[0227] In Table 9, each time point represents the mean ± SD of the percentage of repellency compared to the untreated arm for three different human volunteers. In the untreated arm, 474.8 mosquitoes landed in the Aedes aegypti experiment using 3,6-dimethyl-3a,4,5,6,7,7a-hexahydro-3H-1-benzofuran-2-one. In the untreated arm, 33.8 mosquitoes landed in the An. gambiae experiment using 3,6-dimethyl-3a,4,5,6,7,7a-hexahydro-3H-1-benzofuran-2-one. For human volunteers, the test was stopped when the repellency rate fell below 90%, and nd is indicated if no measurements were taken.

[0228] [Table 11]

[0229] 2.3 Results of the tick worm plate assay The three Cs tested 10 The unsaturated lactones were effective in repelling Ixodes ricinus ticks. As shown in Table 10, at a concentration of 1%, all three compounds repelled all ticks tested, i.e., preventing 12 ticks from walking up and finding a place to settle. 6-pent-3-enyloxan-2-one and 6-pent-2-enyloxan-2-one, tested at higher particle sizes (see Table 10), already reached this 100% repellent efficacy at lower doses, i.e., 0.2% and 0.089%, respectively. These two unsaturated C 10 δ-lactone repelled more than 75% even at a lower concentration of 0.04% (see Table 10).

[0230] In Table 10, a control (0 mg / mL) was created using pure ethanol (used as a solvent) applied to a warm plate. nd indicates that this particular concentration was not tested.

[0231] [Table 12]

Claims

1. A compound selected from the group consisting of the following formulas: 【Chemical 1】 wherein R1 is hydrogen or a straight or branched C １ ~C １５ represents a hydrocarbon group, wherein R2 is hydrogen or a straight or branched C １ ~C １５ represents a hydrocarbon group, or wherein R1 and R2 together form a cycloalkyl, cycloalkenyl, or aryl ring optionally substituted with one or more methyl or ethyl groups; In the formula, n is an integer from 1 to 3; wherein R3 is hydrogen or a straight or branched C １ ~C １５ represents a hydrocarbon group, An arthropod control composition comprising a compound in which the dotted line in formula (I) indicates that the double bond can be present at any position on the lactone ring.

2. 2. The composition of claim 1, wherein n is an integer of 1 or 2, preferably 1.

3. The compound of formula (I) is of the formula 【Chemistry 2】 3. The composition of claim 1 or 2, selected from the group consisting of:

4. The compound of formula (I) is of the formula 【Chemistry 3】 The composition of claim 3 selected from the group consisting of:

5. R1 and R3 are hydrogen; R2 is a straight or branched C １ ~C １５ represents a hydrocarbon group, or R2 is C ７ ~C １０ 5. The composition according to claim 1, wherein the hydroxyl group is a hydrocarbon group.

6. R2 is a straight-chain or branched C having one unsaturation ８ ~C １２ The composition of claim 5 , wherein the hydrocarbon group is a hydrocarbon group.

7. The compound is 5-but-3-enyloxolan-2-one, 5-pent-1-enyloxolan-2-one, 5-pent-2-enyloxolan-2-one, 5-pent-3-enyloxolan-2-one, 5-hex-1-enyloxolan-2-one, 5-hex-2-enyloxolan-2-one, 5-hex-3-enyloxolan-2-one, 5-hex-4-enyloxolan-2-one, 5-hex-5-enyloxolan-2-one, 5-oct-1-enyloxolan-2-one, 5-oct-2-enyloxolan-2-one, 5- Oct-3-enyloxolan-2-one, 5-oct-4-enyloxolan-2-one, 5-oct-5-enyloxolan-2-one, 5-oct-6-enyloxolan-2-one, 5-oct-7-enyloxolan-2-one, 5-[octa-1,5-dienyl]oxolan-2-one, 6-pent-2-enyloxan-2-one, 6-pent-3-enyloxan-2-one, 6-hex-2-enyloxan-2-one, 6-hex-3-enyloxan-2-one, 6-hex-4-enyloxan-2-one, 6-(hex-3-enyl)oxan-2-one 3-(4-hexen-1-yl)tetrahydro-2H-pyran-2-one, 3-buta-1,3-dienyl-4-pentyloxetan-2-one, 7-but-3-enyloxepan-2-one, 7-pent-4-enyloxepan-2-one, 2-pentyl-2H-furan-5-one, 5-pentyl-3,4-dihydro-2H-pyran-2-one, 5-hexyl-3,4-dihydro-2H-pyran-2-one, 5-heptyl-3,4-dihydro-2H-pyran-2-one, 5-(4-hexen-1-yl)-3-methyldihydro-2(3H)-furanone, 5-(3-hexen-1-yl)-3-methyldihydro-2(3H)-furanone, ) 3-methyldihydro-2(3H)-furanone, 4-methyl-5-pentyloxolan-2-one, 5-hexyl-5-methyloxolan-2-one, 5-hex-3-enyl-5-methyloxolan-2-one, 1-oxaspiro[4.5]decan-2-one, 3,6-dimethyl-3a,4,5,6,7,7a-hexahydro-3H-1-benzofuran-2-one, 3-propylidene-2-benzofuran-1-one, 5-[(E)-oct-5-enyl]oxolan-2-one, 5-[(Z)-oct-5-enyl]oxolan-2-one, 5-[(1E,The composition according to any one of claims 1 to 6, wherein the hydroxybenzoate is selected from the group consisting of 4,4,7a-trimethyl-3a,5-dihydro-3H-1-benzofuran-2-one, 4,4,7a-trimethyl-3a,5-dihydro-3H-1-benzofuran-2-one, and 4,4,7a-trimethyl-3a,5-dihydro-3H-1-benzofuran-2-one, and any combination thereof.

8. 8. The composition of claim 7, wherein the compound is selected from the group consisting of 5-hex-3-enyloxolan-2-one, 6-pent-2-enyloxan-2-one, 6-pent-3-enyloxan-2-one, 4-methyl-5-pentyloxolan-2-one, 5-hexyl-5-methyloxolan-2-one, 1-oxaspiro[4.5]decan-2-one, 3,6-dimethyl-3a,4,5,6,7,7a-hexahydro-3H-1-benzofuran-2-one, and 3-propylidene-2-benzofuran-1-one, and any combination thereof.

9. The composition of claim 1 , wherein the composition further comprises at least one fragrance ingredient.

10. 10. The composition according to any one of claims 1 to 9, wherein the composition comprises the compound in an amount of 0.00032 to 20% by weight, preferably 0.001 to 10% by weight, more preferably 0.5 to 1% by weight, based on the total weight of the composition.

11. 11. The composition according to any one of claims 1 to 10, wherein the arthropod is an insect, preferably a mosquito, or wherein the arthropod is an arachnid, preferably a tick.

12. N,N-Diethyl-3-methylbenzamide (DEET), Ethyl butylacetylaminopropionate (IR3535); Paramenthan-3,8-diol (PMD); 1-(1-methylpropoxycarbonyl)-2-(2-hydroxyethyl)piperidine (Picaridin); Chinese cedarwood oil, Texas cedarwood oil, Virginia cedarwood oil, Cinnamon oil, Citronella oil, Cornmint oil, Java citronella (Cymbopogon winterianus) oil fractionated and hydrated, Decanoic acid, Eucalyptus citriodora (Eucalyptus Citriodora hydrated cyclized oil, eugenol, garlic oil, geraniol, geranium oil, lavender oil, Lavandula hybrida oil, lavandin oil, lemon oil, lemongrass oil, neem extract, metofluthrin, cis- and trans-p-menthane-3,8-diol mixture, N,N-diethyl-meta-toluamide, nonanoic acid, rosemary oil, thyme oil, wintergreen oil, 2,3,4,5-bis(butyl-2-ene)tetrahydrofurfural (MGK Repellent 11), cineole, cinnamaldehyde, citronellal, citronellol, coumarin, dibutyl phthalate, diethyl phthalate, dimethyl anthranilate, dimethyl phthalate, ethyl vanillin, eucalyptus oil, hydroxycitronellal, lime oil, limonene, linalool, methyl anthranilate, mint oil, myrcene, neem oil, sabinene, β-caryophyllene, (1H-indol-2-yl)acetic acid, anethole, anise oil, basil oil yl, bay oil, camphor, ethyl salicylate, evergreen oil (pine oil), clove oil, nootkatone, 2-undecanone, sulcatone, (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate (d-tetramethrin), 3-allyl-2-methyl-4-oxocyclopent-2-enyl-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate (d-allethrin), α-cyano-3-phenoxybenzyl, 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (cypermethrin), 2-methyl-4-oxo-3-(prop-2-ynyl)cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate (prallethrin), acetamiprid, azadirachtin, bendiocarb, bifenthrin, boric acid, chlorpyrifos, deltamethrin, diazinon, dichlorovos, eugenol, fipronil, imidacloprid, malathion, maltodextrin, metofluthrin, nicotine, permethrin Methrin, pyrethrins, pyrethroids, rotenone, silicon dioxide (diatomaceous earth), S-methoprene, spinosad (spinosyn A), spinosyn D, tetramethrin, transfluthrin, 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one, 3-butylidene-2-benzofuran-1-one, 4-ethenyl-2-methoxyphenol, konjac green oil, labdanum extract (Cistus species), 5-pentylxolan-2-one, chromen-2-one, 3,7-dimethylocta-2,6-dienal, 4-hydroxy-3-methoxybenzaldehyde, 2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one, spearmint (Mentha spicata oil, 6-hexyloxan-2-one, 5-methyl-2-propan-2-ylcyclohexyl acetate, Nigella damascena oil, 2-phenylethanol, 6-pentyloxan-2-one, (4-methoxyphenyl)methyl acetate, clove (Syzygium aromaticum) oil, 3,4,4a,5,6,7,8,8a-octahydrochromen-2-one, 3,7,7-trimethylbicyclo[4.1.0]hept-3-ene, 2-phenylethyl 2-methylpropanoate, methyl 2-(3-oxo-2-pent-2-enylcyclopentyl)acetate, 4-(2-methoxypropan-2-yl)-1-methylcyclohexene, peppermint (Mentha piperita) oil, 2-methoxy-4-[prop-1-enyl]phenol, 2-methyl-3-(4-propan-2-ylphenyl)propanal, (4-methoxyphenyl)methanol, 2,3-dihydro-1H-indene-2-carbonitrile, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2,5-di Methyl-2,3-dihydro-1H-inden-2-yl)methanol, (4aRS,9bRS)-4a,7-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2RS,4aRS,9bRS)-2,4a,7-trimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2RS,4aSR,9bSR)-2,4a,7-trimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][ 1,3]dioxin, (2-methyl-1,3-dihydroinden-2-yl)methanol, 2,3-dihydro-1H-inden-2-ylmethanol, (2RS,4RS,4ASR,9BRS)-2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2RS,4aRS,9bSR)-2-methyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2RS,4aSR,9bRS)-2-methyl -4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (4aRS,9bSR)-2,2-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2,4,6-trimethyl-2,3-dihydro-1H-inden-2-yl)methanol, 5-(tert-butyl)1,3-dihydrospiro[indene-2,3′-oxetane], (2RS,4RS,4ARS,9BSR)-2,4-dimethyl-4,4a,5,9b-Tetrahydroindeno[1,2-d][1,3]dioxin, 4A,8-dimethyl-indano[1,2-d]-1,3-dioxan-2-one, 1-(2,5-dimethyl-2,3-dihydro-1H-inden-2-yl)ethanone, (5-methyl-2,3-dihydro-1H-inden-2-yl)methanol, (4aRS,9bSR)-8-methyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (2RS,4aRS,9bSR)-2-ethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxy Indene, (2RS,4aSR,9bRS)-2-ethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2R,4aS,9bS)-2,4a,8-trimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, 1-(2,5-dimethyl-2-indanyl)-1-ethanol, (2,5-dimethyl-2,3-dihydro-1H-inden-2yl)methanol, (2RS,4aRS,9bSR)-2,8-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2RS,4aSR,9bRS)-2,8-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2RS,4aSR,9bSR)-2,4a-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (4aRS,9bRS)-4a,8-dimethyl-4,4a, 5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, 1-(2,4,5-trimethyl-2,3-dihydro-1H-inden-2-yl)ethenone, (2RS,4aRS,9bSR)-2-ethyl-8-methyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (2RS,4aSR,9bRS )-2-ethyl-8-methyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, (4aRS,9bRS)-2,2,4a,8-tetramethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxine, 5-tert-butyl-indan-2-spiro-3'-oxetane, (2,6- Dimethyl-1,2,3,4-tetrahydro-2-naphthalenyl)methanol, (4aRS,9bRS)-2,2,4a trimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxin, (4aRS,9bRS)-2,2,4a,7-tetramethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3] dioxin, 3-(3 / 4-ethylcyclopent-1-en-1-yl)-2-methylpropanal, 3-(3 / 4-propylcyclopent-1-en-1-yl)-2-methylpropanal, 3-(3 / 4-butylcyclopent-1-en-1-yl)-2-methylpropanal, 3-(3 / 4-isopropylcyclopent-1-en-1-yl)-2-methylpropanal, 3-(3 / 4-(sec-butyl)cyclopent-1-en-1-yl)-2-methylpropanal, 3-(3 / 4-(tert-butyl)cyclopent-1-en 3-(4-(2-hydroxy-2-methylpropyl)phenyl)propanal, 3-(4-tert-butyl-2-methylphenyl)propanal, 3-(4-tert-butylphenyl)propanal, 3-(3-propan-2-ylphenyl)butanal, 3-(4-methoxyphenyl)-2-methylpropanal, 2,6-dimethoxy-4-[prop-1-enyl]phenol, 4-allyl-2,6-dimethoxyphenol phenol, 1,2,3-trimethoxy-5-[1-propen-1-yl]benzene, 1,2,3-trimethoxy-5-propylbenzene, 1,2,4-trimethoxybenzene, 2,6-dimethoxy-4-propylphenol, 2,6-dimethoxy-4-methylphenol, 3-(3,4,5-trimethoxyphenyl)propen-2-oic acid, 2-(4-hydroxy-3-methoxyphenyl)acetic acid, methyl 3-(3,4-dimethoxyphenyl)-2-methylpropanoate, (2,3-dimethoxyphenyl)methanol, 2,3,4-trimethoxybenzal aldehyde, 3,4,5-trimethoxybenzaldehyde, 2-ethoxy-4-(methoxymethyl)phenol, 2-ethoxy-4-(ethoxymethyl)phenol, 1,2-dimethoxy-4-prop-1-enylbenzene, 1,2,3-trimethoxy-5-methylbenzene, 2,6-dimethoxy-4-methylphenol, 1-(2,3,4-trimethoxyphenyl)ethanone, 7-methyl-1,5-benzodioxepin-3-one, 1,2-dimethoxy-3-prop-1-enylbenzene, 1,2,3-trimethoxy-5-propylbenzene, 2,3,The composition of any one of claims 1 to 11, further comprising an arthropod control co-ingredient selected from the group consisting of 4-trimethoxybenzonitrile, 3-ethoxy-4-methoxybenzaldehyde, 2,3,4-trimethoxyphenol, 1-(4-hydroxy-3-methoxyphenyl)ethanone, 2-methoxy-4-(4-methylideneoxan-2-yl)phenol, 4-(3,6-dihydro-4-methyl-2H-pyran-2-yl)-2-methoxy-phenol, 3-(4-isopropyl-2-methylphenyl)propanal, 3-(2-isopropyl-4-methylphenyl)propanal, and mixtures thereof.

13. 13. A method for controlling arthropods, preferably insects, comprising directly contacting or contacting the arthropods with a vapor of a composition according to claims 1 to 12.

14. 13. Use of a composition according to any one of claims 1 to 12 for controlling arthropods.

15. A consumer product comprising the composition of claims 1 to 12.

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