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(12) Patent Application Publication (10) Pub. No.: US 2006/0235071 A1 Cantrell Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2006/0235071 A1 Cantrell Et Al US 20060235071A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2006/0235071 A1 Cantrell et al. (43) Pub. Date: Oct. 19, 2006 (54) NOVEL CLERODANES AND METHODS FOR REPELLING ARTHROPODS (76) Inventors: Charles L. Cantrell, Oxford, MS (US); Jerome A. Klun, Potomac, MD (US); Stephen O. Duke, Oxford, MS (US) Correspondence Address: O USDA, ARS, OTT 56O1 SUNNYSDEAVE RM 4-1159 BELTSVILLE, MD 20705-5131 (US) (21) Appl. No.: 11/374,866 in which R" is H. halogen, formyl, a straight chain or branched Ca Saturated alkyl, a straight chain or branched (22) Filed: Mar. 14, 2006 C, unsaturated alkyl, or an aryl containing 6-10 carbon atoms in the ring skeleton thereof, wherein R' is unsubsti Related U.S. Application Data tuted or substituted with one or more substituents, which are (60) Provisional application No. 60/672.849, filed on Apr. the same or different, selected from the group consisting of 19, 2005. oxo (=O), OR, COR, and OC(O)R’, wherein R is H, a straight chain or branched Co Saturated alkyl, a straight Publication Classification chain or branched Co unsaturated alkyl, or an aryl com prising 6-10 carbon atoms in the ring skeleton thereof. (51) Int. Cl. wherein R is unsubstituted or substituted with one or more AOIN 43/20 (2006.01) Substituents selected from the group consisting of halogen, AOIN 37/00 (2006.01) amino, hydroxyl, oxo (=O), thio, cyano and nitro; option AOIN 3L/00 (2006.01) ally a carrier, optionally an arthropod repellant, and option ADIN 43/24 (2006.01) ally an insecticide. Preferably the compound is 13,14,15, (52) U.S. Cl. ........................... 514/475; 514/559; 514/729 16-tetranorclerod-3-en-12-all (callicarpenal), 13, 14,15, 16 tetranorclerod-3-en-12-ol, 13,14,15, 16-tetranorclerod-3-en (57) ABSTRACT 12-oic acid, B-epoxycallicarpenal, C.-epoxycallicarpenal, or A method for repelling arthropods involving treating a mixtures thereof. Also a compound of the above formula. Subject or an object with an arthropod repelling composition Also an arthropod repellant composition containing an containing an arthropod repelling effective amount of at arthropod repelling effective amount of at least one of the least one clerodane of the formula compounds of the above formula and a carrier. Patent Application Publication Oct. 19, 2006 Sheet 1 of 4 US 2006/0235071 A1 s e e ar ea ar 4. 2 O-humulene humulene epoxide II 5 2 SS S ss 18 4. callicarpenal intermedeol 14 spathulenol Fig. 1 Patent Application Publication Oct. 19, 2006 Sheet 2 of 4 US 2006/0235071 A1 C. amenicana Oil C. japOnica Oil 200000 C E 150000 2 A 100000 B CD D 50000 O 20 25 30 35 40 Retention Time (min) Fig. 2 Patent Application Publication Oct. 19, 2006 Sheet 3 of 4 US 2006/0235071 A1 18 Colony 1 16 14 12 1 0.8 0.6 04 0.2 S. in Victa S. richter Hybrid S. in Victa S. richter Hybrid Octanoic acid 3 Callicarpenal Fig. 3 Patent Application Publication Oct. 19, 2006 Sheet 4 of 4 US 2006/0235071 A1 18 16 14 1.2 1 O.8 O6 0.4 0.2 S. in Victa S. nichteni Hybrid 16 14 12 O.8 0.6 0.4 0.2 S. nVicta S. richter Hybrid O Octanoic acid : Intermedeo Fig. 4 US 2006/0235071 A1 Oct. 19, 2006 NOVEL CLERODANES AND METHODS FOR concern has recently emerged about the potential toxicity of REPELLING ARTHROPODS DEET to children. Recently the US Environmental Protec tion Agency (EPA) determined that it would no longer allow REFERENCE TO RELATED APPLICATION child safety claims on labels for DEET-containing products. 0001) This application claims the benefit of U.S. Provi 0005 Thus there is a need for alternatives to chemicals sional Application No. 60/672,849, filed 19 Apr. 2005, Such as DEET to use against insects such as mosquitoes. which is incorporated herein by reference in its entirety. SUMMARY OF THE INVENTION BACKGROUND OF THE INVENTION 0006. In accordance with the present invention there is 0002 The present invention relates to a method for provided a method for repelling arthropods involving treat repelling arthropods involving treating a subject or an object ing a subject or an object with an arthropod repelling with an arthropod repelling composition containing an composition containing an arthropod repelling effective arthropod repelling effective amount of at least one com amount of at least one compound having the formula pound having the formula O O wherein R' is H. halogen, formyl, a straight chain or wherein R' is H. halogen, formyl, a straight chain or branched Ca Saturated alkyl, a straight chain or branched branched Ca Saturated alkyl, a straight chain or branched C, unsaturated alkyl, or an aryl containing 6-10 carbon C, unsaturated alkyl, or an aryl containing 6-10 carbon atoms in the ring skeleton thereof, wherein R' is unsubsti atoms in the ring skeleton thereof, wherein R' is unsubsti tuted or substituted with one or more substituents, which are tuted or substituted with one or more substituents, which are the same or different, selected from the group consisting of the same or different, selected from the group consisting of oxo (=O), OR, COR, and OC(O)R’, wherein R is H, a oxo (=O), OR, COR, and OC(O)R’, wherein R is H, a straight chain or branched Co Saturated alkyl, a straight straight chain or branched Co Saturated alkyl, a straight chain or branched Co unsaturated alkyl, or an aryl com chain or branched Co unsaturated alkyl, or an aryl com prising 6-10 carbon atoms in the ring skeleton thereof. prising 6-10 carbon atoms in the ring skeleton thereof. wherein R is unsubstituted or substituted with one or more wherein R is unsubstituted or substituted with one or more Substituents selected from the group consisting of halogen, Substituents selected from the group consisting of halogen, amino, hydroxyl, oxo (=O), thio, cyano and nitro; or amino, hydroxyl, oxo (=O), thio, cyano and nitro; or mixtures thereof optionally a carrier, optionally an arthro mixtures thereof, optionally a carrier, optionally an arthro pod repellant, and optionally an insecticide. Preferably the pod repellant, and optionally an insecticide. Preferably the compound is callicarpenal, 13.14.15, 16-tetranorclerod-3-en compound is 13,14,15, 16-tetranorclerod-3-en-12-all (calli 12-ol. 13,14,15, 16-tetranorclerod-3-en-12-oic acid, B-ep carpenal), 13,14,15, 16-tetranorclerod-3-en-12-ol. 13,14,15, oxycallicarpenal, C-epoxycallicarpenal, or mixtures thereof. 16-tetranorclerod-3-en-12-oic acid, B-epoxycallicarpenal, C-epoxycallicarpenal, or mixtures thereof. The present 0007 Also in accordance with the present invention there invention also relates to compounds of the above formula. is provided compounds of the above formula. Furthermore, the present invention relates to an arthropod repellant composition containing an arthropod repelling 0008 Still also in accordance with the present invention effective amount of at least one of the compounds of the there is provided an arthropod repellant composition con above formula and a carrier. taining an arthropod repelling effective amount of at least one of the compounds of the above formula and a carrier. 0003 Insect repellants are widely used throughout the United States and throughout the world. In some regions, the BRIEF DESCRIPTION OF THE DRAWINGS use of insect repellants is critical to avoiding or reducing the occurrence of disease carried by insects. For example the 0009 FIG. 1 shows compounds isolated from Callicarpa Centers for Disease Control (CDC) receives nearly 10,000 americana and C. japonica. reports of Lyme disease (transmitted by deer ticks) and 1,000 reports of encephalitis (transmitted by mosquitoes) 0010 FIG. 2 shows GC-MS (Gas Chromatography-Mass annually. Spectroscopy) total ion chromatograms for C. americana and C. japonica essential oil extracts (A=C-humulene; 0004 Currently, the most common insect repellent is B=humulene epoxide II: C=intermedeol ((4S,5S,7R,10S)- N,N-diethyl-meta-toluamide (DEET). DEET was designed eudesm-11-en-4-ol); D=callicarpenal (13,14,15, 16-tetran to be applicable to the skin of Subjects, and is designed to orclerod-3-en-12-al); E=spathulenol ((1R,4S.5R.6R,7R)- repel rather than kill insects. Although in use for some time, aromadendr-10(14)-en-4-ol)). US 2006/0235071 A1 Oct. 19, 2006 0011 FIG. 3 shows head-to-head comparison on the carpenal, or mixtures thereof. Also a compound of the above repellency of callicarpenal and octanoic acid against fire ant formula. Also an arthropod repellant composition containing workers in two choice bioassays (n=5). Anasterisk indicates an arthropod repelling effective amount of at least one of the the repellency of callicarpenal was significantly greater than compounds of the above formula and a carrier. that of octanoic acid (Paired t-test). 0014. The method can therefore be used for repelling 0012 FIG. 4 shows head-to-head comparison on the harmful or troublesome arthropods such as blood-sucking repellency of intermedeol and octanoic acid against fire ant and biting insects, ticks and mites. workers in two choice bioassays (n=5). Anasterisk indicates 00.15 Blood-sucking insects include mosquitoes (for the repellency of intermedeol was significantly greater than example Aedes, Culex and Anopheles species), including but that of octanoic acid (Paired t-test). not limited to Tiger mosquitoes, Aedes aboriginis, Aedes DETAILED DESCRIPTION OF THE Aegypti, Aedes albopictus, Aedes cantator; Aedes Sierrensis, Aedes solicitans, Aedes squamiger, Aedes Sticticus, Aedes INVENTION vexans, Anopheles quadrimaculatus, Culex pipiens, and 0013 A method for repelling arthropods is disclosed Culex quinquefax'ciatus, owl gnats (Phlebotoma), blackfly involving
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