We synthesized or re-synthesized a large series of 2H-1,5-benzodioxepin-3(4H)-ones 9 (Scheme 1), 4,5-dihydro-1-benzoxepin-3(2H)-ones 10 (Schemes 3 and 4) and 5,6,8,9-tetrahydro-7H-benzocyclohepten-7-ones 11 (Schemes 5 and 6), since the lead compound for the olfactory note of perfumes based on marine accords is a well-known benzodioxepinone named Calone 1951 (9b). We meticulously described the odor profile of each synthesized compound and discussed relevant structure -odor relationships (Tables 1 -3). In particular, we revealed a correlation between the conformation of the seven-membered ring and the activities of these compounds (Table 4 and Fig. 3). We also clarified the effect of the position and the size of the alkyl substituent at the aromatic ring.

By a simple methodology, we have synthesized 68 carboxamides, with structural analogy to the most efficient mosquitoes repellent DEET (N,N-diethyl-m-toluamide, 9). Eight of them have very promising olfactory profiles. In addition, 34 carboxamides have been tested for their repellency properties against three breeds of cockroach; six of them are excellent in this domain. Two of these, the 2-ethyl-N-isopropyl-N-methylbutanamide and N,N-diallyl-2-ethylbutanamide combine both the positive aspects, and are thus very good candidates for use in functional perfumery, and more particularly in home-care formulations.