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) (51) International Patent Classification: Published: — with International Search Report (Art. 21(3)) (21) International Appl ) ( (51) International Patent Classification: Published: A01N 31/02 (2006.01) C07C 69/04 (2006.01) — with international search report (Art. 21(3)) A01N 37/02 (2006.01) C07D 305/14 (2006.01) A01N 43/30 (2006.01) C07D 319/08 (2006.01) C07C 35/32 (2006.01) A01P 1 7/00 (2006.01) (21) International Application Number: PCT/EP2020/064976 (22) International Filing Date: 29 May 2020 (29.05.2020) (25) Filing Language: English (26) Publication Language: English (30) Priority Data: 19177668. 1 31 May 2019 (3 1.05.2019) EP (71) Applicant: FIRMENICH SA [CH/CH]; 7, Rue de la Bergere, 1242 Satigny (CH). (72) Inventors: CHAPPUIS, Charles; Firmenich SA, 7, Rue de la Bergere, 1242 Satigny (CH). HARRACA, Vincent; Firmenich SA, 7, Rue de la Bergere, 1242 Satigny (CH). BANDERA, Monica; Firmenich SA, 7, Rue de la Bergere, 1242 Satigny (CH). (74) Agent: BAUMGARTNER HARRIS, Pauline; Firmenich SA, 7, Rue de la Bergere, 1242 Satigny (CH). (81) Designated States (unless otherwise indicated, for every kind of national protection available) : AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, WS, ZA, ZM, ZW. (84) Designated States (unless otherwise indicated, for every kind of regional protection available) : ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, Cl, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). Declarations under Rule 4.17: — as to applicant's entitlement to apply for and be granted a patent (Rule 4.17(H)) — of inventorship (Rule 4.17(iv)) (54) Title: ARTHROPOD CONTROLLING COMPOSITION (57) Abstract: The present invention relates to an arthropod controlling composition comprising a compound according to formula (I), methods and uses to control arthropods as well as arthropod controlling articles comprising the same. Arthropod Controllinq Composition Technical Field The present invention relates to an arthropod controlling composition comprising a compound according to formula (I), methods and uses to control arthropods as well as arthropod controlling articles comprising the same. Backqround Many mammals, including humans, are suffering from the action of arthropods. Some arthropods, such as for example mosquitoes and ticks, are not desirable for vertebrates such as mammals and in particular human subjects as they bite and, consequently, cause itching, transmission of diseases and/or germs or may be the cause for other diseases and/or conditions. Arthropod control compositions include active substances and when applied to skin, clothing, or other surfaces, they may discourage arthropods from landing or climbing on that surface. Arthropod control agents help preventing and controlling the outbreak of arthropod- borne diseases, such as malaria, etc. The prior art describes structurally diverse arthropod control agents, such as for example A/,/V-diethyl-3-methylbenzamide (also known as DEET) or ethyl butylacetylaminopropionate (also known as insect repellent 3535, IR3535). Some of the known arthropod control agents, however, have certain drawbacks, such as being irritant to the skin, to a subject, in particular of children, and/or have negative olfactive properties, such as bad smell. There is a need to provide arthropod controlling compounds and compositions which use limited amount of or are totally free from irritant arthropod control agents. EP 1 022 265 describes the olfactory properties of some compounds used in compositions according to the present invention and their use as perfuming ingredients providing odoriferous characteristics of the lily of the valley type, but does not disclose or suggest said compounds as having an arthropod controlling effect. No prior art discloses or suggests the compounds according to the present invention as having an arthropod controlling effect. Description of the Figures Figure 1: In-vitro repulsion of mosquitoes Aedes aegypti measured against different dilutions of (2,5-dimethyl-2,3-dihydro-1 /-/-inden-2yl)methanol in the K&D test. Figure 2 : In-vivo repulsion of mosquitoes Aedes aegypti measured against different dilutions of (2,5-dimethyl-2,3-dihydro-1 /-/-inden-2yl)methanol in the K&D test. Figure 3 : Numbers of mosquitoes Aedes aegypti landing on the Warm Body with different dilutions of DEET (circle plain line), IR3535 (triangle dashed line) or (2,5-dimethyl-2,3-dihydro-1 FI-inden-2yl)methanol (cross, dotted line) applied on it. Figure 5 : In-vitro repulsion of mosquitoes Aedes aegypti measured in the Warm Body Assay against two different perfumes containing 33% and 10% of (2,5- dimethyl-2,3-dihydro-1 FI-inden-2yl)methanol (square; black & triangle; black respectively), two reference compounds: DEET (diamond; gray), IR3535 (circle; gray) and the solvent ethanol (no index; black). Figure 4 : In-vitro repulsion overtime of mosquitoes Aedes aegypti measured in the Warm Body Assay against two different perfumes containing 33% and 6.5% of (2,5-dimethyl-2,3-dihydro-1 FI-inden-2yl)methanol (square & triangle respectively) plus 7.5% or 12.5% of IR3535 (gray and black respectively) in an aqueous phase. Figure 6 : In-vitro repulsion of mosquitoes Aedes aegypti measured in the Warm Body Assay 4h post application against two different blends made of 0.25% or 1% of perfume 1a containing 33% of (2,5-dimethyl-2,3-dihydro-1 Fl-inden- 2yl)methanol (light and dark gray respectively) plus 12.5% of IR3535 in an aqueous phase. Figure 7 : In-vitro repulsion of mosquitoes Aedes aegypti measured in the Warm Body Assay against a blend (gray) containing two perfumery ingredients with arthropods’ controlling properties ((2,5-dimethyl-2,3-dihydro-1 Fl-inden- 2yl)methanol + methyl ( 1 R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate [ 1 :1]) or methyl ( 1 R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate (black) used as reference. All stimuli were diluted in ethanol at 0.001 6%, 0.04% and 1% (w/w). Figure 8 : In-vitro repulsion of mosquitoes Aedes aegypti measured in the Warm Body Assay against seven different compounds at 3 different concentrations: DEET (gray diamond) & IR3535 (gray circle) used as references, 4a,8-dimethyl- indano[1 ,2-d]-1 ,3-dioxan-2-one (black square), (2,4,6-trimethyl-2,3-dihydro- 1/-/-inden-2-yl)methanol (black diamond), 5-ethyl-2-methyl-2-indanmethanol (black triangle), 1-(2,5-dimethyl-2-indanyl)-1 -ethanol (black circle) and (2,5- dimethyl-2,3-dihydro-1 FI-inden-2yl)methanol (black cross). Figure 9 : In-vitro repulsion of mosquitoes Aedes aegypti measured in the Warm Body Assay against seven different compounds at 3 different concentrations: DEET (gray diamond) & IR3535 (gray circle) used as references, (2,5-dimethyl-2- indanyl)methyl formate (black square), (2,5-dimethyl-2,3-dihydro-1 H-inden-2- yl)methyl methyl ether (black diamond), 2,5-dimethyl-2,3-dihydro-1 H-indene-2- carboxylic acid (black triangle), (2,5-dimethyl-2,3-dihydro-1 H-inden- 2yl)methanol (black circle) and 5-isopropyl-2-methyl-2-indanmethanol (black cross) Figure 10 : In-vitro repulsion of mosquitoes Aedes aegypti measured in the Warm Body Assay against eleven different compounds at 3 different concentrations: DEET (gray diamond) & IR3535 (gray circle) used as references, ( 1 RS,2SR)-2- (hydroxymethyl)-2,6-dimethyl-2,3-dihydro-1 H-inden-1 -ol (black circle), 5-tert- butyl-2-methyl-2-indanmethanol (black square), a blend of ( 1 RS,2RS)-2-((2- methoxypropan-2-yloxy)methyl)-2,6-dimethyl-2,3-dihydro-1 H-inden-1 -ol + ( 1 RS,2SR)-2-((2-methoxypropan-2-yloxy)methyl)-2,6-dimethyl-2,3-dihydro-1 I- inden-1-ol (black diamond) and a blend of ( 1 RS,2RS)-2-(hydroxymethyl)-2,6- dimethyl-2,3-dihydro-1 H-inden-1 -ol + ( 1 RS,2SR)-2-(hydroxymethyl)-2,6- dimethyl-2,3-dihydro-1 H-inden-1 -ol (black triangle). Figure 11 In-vitro repulsion of ticks Ixodes ricinus measured in the Warm Body Assay against ethanol (control; black), (2,4,6-trimethyl-2,3-dihydro-1 FI-inden-2- yl)methanol (Ingredientl ) (2,5-dimethyl-2,3-dihydro-1 FI-inden-2yl)methanol (Ingredient2) and N,N-diethyl-3-methylbenzamide (DEET) diluted in ethanol at 0.4 mg/ml_ (light gray) and 10 mg/ml_ (dark gray ; mean values of 2-5 replicates of n=1 1- 12 ticks). Detailed description The present invention relates to an arthropod, preferably insect, control composition comprising - a compound of formula (I) in the form of any one of its stereoisomers or a mixture thereof, and wherein n represents 1 or 2 ; X represents a CH2, CH(OH) or C=N-OH group; R1 represents a CN, CHR7 OR8 or a COR9 group, R7 being a hydrogen atom or a methyl group, 8 R being a hydrogen atom, a C1-3 hydrocarbon group, optionally substituted by a 9 and hydroxyl or a C1-3 alkoxy group, a C3-10 trialkylsilyl group, or a COR group, 9 R being a hydrogen atom, a hydroxyl group, a C1-3 alkoxy group, a C1-8 hydrocarbon group, or a phenyl, each optionally substituted by one to three groups selected amongst a C1-3 alkyl, alkoxy or amine group; 2 R represents a hydrogen atom or a methyl, ethyl or CH2OH group; 3 R represents a hydrogen atom or a C1-5 hydrocarbon group or a C1-3 alkoxyl group; and 4 5 6 R , R and R represents, independently from each other, a hydrogen atom or a C1-5 alkyl or C2-5 alkenyl group; or 1 2 R and R when taken together represent a CH2 -0-C(=0)-0, CH2 -0-CH 2 - 0 or CH2 -0- CH2 group; or 1 10 10 X and R when taken together represent a CH-O-C(=O)-O-C(R )2 or CH-O-C(R ) 2- 10 10 0 -C(R ) 2 group wherein R , independently from each other, represents a hydrogen atom or a C1-3 alkyl group; - optionally, at least one arthropod control co-ingredient.
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