International Flavors & Fragrances Inc.

University of Florida Research Foundation Inc

Other

The Procter Gamble Company

Anubhav P Narula

Marie R Hanna

Jerry F Butler

Craig B Warren

Anna B Marin

Richard M Boden

William L Schreiber

Braja D Mookherjee

Johan Smets

Richard A Wilson

Robert P Belko

Michael G Monteleone

Richard Anthony Weiss

Anthony T Levorse, Jr

Edward Mark Arruda

Charles E Beck

Matthew J McGinnis

Futoshi Fujioka

An Pintens

Myrna L Hagedorn

Adam P Closson

Hugo Robert Germain Denutte

Leslie C Smith

Benjamin Amorelli

John J De Virgilio

Takashi Sasaki

Feng Geng

Anton V Ouwerkerk

Carlos Benaim

Jan T Van Elst

Olivier J Gillotin

Franc T Schiet

Vincent F Kuczinski

Anton Van Ouwerkerk

Gary J Mertz

Anthony G Branco

Eleanor Fox

James Anthony Lasome

Heedong Yun

Nicole O'Keefe

Isabelle Guimet

Tingwei Cai

Kathleen E Boardwick

James Joseph Koestler

Leroy P John

William D Gillaspey

Sophia Grojsman

John J DeVirgilio

De Virgilio John J

Charles J Vinals

Peter J Hartong

Francis Charles Thibaudeau

Honorine Hattab

Anthony T Levorse Jr

Described is a method of repelling Musca domestica L.(Diptera:Muscidae), Aedes aegypti, Culex nigripalpus, Aedes atlanticus, Culex salinarius, Aedes vexans, Culex spp., Simulium spp., Psoroferia ferox, Aedes infirmatus, Drosophila melanogaster, Coccinellidae, Anopheles crucians, Psoroferia columbiae, Culicoides spp., Aedes spp. and Haematobia for a finite period of time from a three dimensional space inhabited by at least one of such insect species consisting essentially of the step of exposing a three dimensional space to an effective insect species member repelling concentration and quantity of a dimethyl substituted oxymethyl cyclohexane derivative-containing composition of matter defined according to the structure: ##STR1## The above-stated repellents are described to be useful as such or contained in a polymer which can be a biodegradable polymer such as compositions containing a major proportion of poly(epsilon caprolactone) homopolymers. The above-stated repellents are also useful in conjunction with a washing soap whereby the insect repelling composition is initially admixed with a soap base; the resulting mixture is formulated into a soap article; and the resulting soap article is used in a washing procedure on a member of the mammalian species.

Use of dimethyl substituted oxymethyl cyclohexane derivatives for their

Described is a method for repelling insects by use of oxymethyl cyclohexane derivatives of the structure ##STR1## wherein Z is methylene; n is 0 or 1; each of the wavy lines represents a carbon-carbon single bond or no bond; the dashed line represents a carbon-carbon double bond or a carbon-carbon single bond; each of R.sub.2, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are the same or different and each represents hydrogen or methyl; and R.sub.1 represents hydrogen, acetyl or ethoxycarbonyl with the provisos:

Dimethyl substituted oxymethyl cyclohexane derivatives for their insect

Described are methyl substituted hexahydroindanols and alkyl ethers thereof defined according to the generic structure: ##STR1## wherein R.sub.7 represents hydrogen or C.sub.1 -C.sub.3 alkyl; wherein R.sub.1 represents methyl or ethyl; wherein R.sub.4 represents methyl or hydrogen; and wherein R.sub.2, R.sub.3, R.sub.5 and R.sub.6 each represents methyl or ethyl with the provisos that:

Methyl substituted hexahydroindanols and alkyl ethers thereof,

Described are 1(4'-methylpentyl)-4-substituted ethylcyclohexane derivatives defined according to the structure: ##STR1## wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different hydrogen or methyl; wherein the dashed line represents a carbon carbon single bond or a carbon carbon double bond; wherein the wavy line represents a carbon carbon single bond or a carbon carbon double bond; with the proviso that when the wavy line is a carbon carbon single bond then the dashed line is a carbon carbon single bond; wherein Y represents a moiety selected from the group consisting of: ##STR2## wherein H represents hydrogen, C.sub.1 -C.sub.4 lower alkyl or C.sub.1 -C.sub.2 acyl; and wherein R.sub.1 represents C.sub.1 -C.sub.4 lower alkyl with the additional proviso that when Y is the moiety: ##STR3## then the dashed line is a carbon carbon single bond, and uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, perfumed articles and colognes. Also described are processes for producing the above-mentioned 1(4'-methylpentyl)-4-substituted ethylcyclohexane derivatives as well as intermediates used in said processes.

1(4'-methylpentyl)-4-substituted ethylcyclohexane derivatives,

Described are methyl substituted tetrahydroindane alkyl enol ethers defined according to the structure: ##STR1## wherein R.sub.1 represents methyl or ethyl; wherein R.sub.4 represents methyl or hydrogen; wherein R.sub.2, R.sub.3, R.sub.5 and R.sub.6 each represents methyl or ethyl with the provisos that:

Methyl substituted tetrahydroindane alkyl enol ethers, perfumery uses

Described is a method of repelling Musca domestica L.(Diptera:Muscidae), Aedes aegypti, Culex nigripalpus, Aedes atlanticus, Culex salinarius, Aedes vexans, Culex spp., Simulium spp., Psoroferia ferox, Aedes infirmatus, Drosophila melanogaster, Coccinellidae, Anopheles crucians, Psoroferia columbiae, Culicoides spp., and Aedes spp. for a finite period of time consisting essentially of the step of exposing a three-dimensional space to an effective repelling concentration and quantity of geraniol or a geraniol precursor-containing composition consisting essentially of 50-100% geraniol or a geraniol precursor (e.g., geranyloxy-1,3,2-dioxaborinane, digeranyloxydimethylsilane and geranyl glycosides, for example, geranyl 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside) with the remainder of the composition (if indeed the composition is not 100% geraniol) being a compound selected from the group consisting of citronellol and nerol. The above-stated repellents are described to be useful as such or contained in a polymer which can be a biodegradable polymer such as compositions containing a major proportion of poly(epsilon caprolactone) homopolymers.

Insect repellent compositions and methods for using same

Described is a method for repelling insects by use of oxymethyl cyclohexane derivatives of the structure ##STR1## wherein Z is methylene; n is 0 or 1; each of the wavy lines represents a carbon-carbon single bond or no bond; the dashed line represents a carbon-carbon double bond or a carbon-carbon single bond; each of R.sub.2, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are the same or different and each represents hydrogen or methyl; and R.sub.1 represents hydrogen, acetyl or ethoxycarbonyl with the provisos: (i) that n is 1 and each of the wavy lines represents a carbon-carbon single bond when R.sub.1, R.sub.2, and R.sub.6, are each hydrogen, R.sub.5, R.sub.7 and R.sub.8 are each methyl and the dashed line is a carbon-carbon single bond; (ii) n is 0 and each of the wavy lines represents no bond when R.sub.5 and R.sub.7 are each hydrogen and R.sub.6 and R.sub.8 are each methyl; (iii) R.sub.2 is methyl only when R.sub.1 is ethoxycarbonyl; and (iv) the dashed line is a carbon-carbon single bond only when R.sub.1 is hydrogen.

Described is a method of repelling Musca domestica L. (Diptera:Muscidae), Aedes aegypti, Culex nigripalpus, Aedes atlanticus, Culex salinarius, Aedes vexans, Culex spp., Simulium spp., Psoroferia ferox, Aedes infirmatus, Drosophila melanogaster, Coccinellidae, Anopheles crucians, Psoroferia columbiae, Culicoides spp., and Aedes spp. for a finite period of time from a three-dimensional space inhabitable by these insects consisting essentially of exposing a three-dimensional space to an effective concentration and quantity of geraniol or a geraniol precursor-containing composition consisting essentially of 50-100% geraniol or a geraniol precursor (e.g., geranyloxy-1,3,2-dioxaborinane, digeranyloxydimethylsilane and geranyl glycosides, for example, geranyl 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside) with the remainder of the composition (if indeed the composition is not 100% geraniol) being a compound selected from the group consisting of citronellol and nerol. The above-stated repellents are described to be useful as such or contained in a polymer which can be a biodegradable polymer such as compositions containing a major proportion of poly(epsilon caprolactone) homopolymers.

Described is a method of repelling Musca domestica L. (Diptera:Muscida), Aedes aegypti, Culex nigripalpus, Aedes atlanticus, Culex salinarius, Aedes vexans, Culex spp., Simulium spp., Psoroferia ferox, Aedes infirmatus, Drosophila melanogaster, Coccinellidae, Anopheles crucians, Psoroferia columbiae, Culicoides spp., Aedes spp. and Haematobia irritans [L.]for a finite period of time from a three-dimensional space inhabited by said insect species consisting essentially of the step of exposing a three-dimensional space inhabited by said insect species to an effective insect species repelling concentration and quantity of at least one dimethyl substituted oxymethyl cyclohexene derivative defined according to the structure: ##STR1## wherein R.sub.2 represents hydrogen or methyl.

Use of dimethyl substituted oxymethyl cyclohexene derivatives for their

Described is a method for attracting the insect species Culex nigripalpus, Aedes atlanticus, Culex salinarius, Aedes vexans, Culex spp., Simulium spp., Psoroferia ferox, Aedes infirmatus, Drosophila melanogaster, Coccinellidae, Anopheles crucians, Psoroferia columbiae, Culicoides spp. and Aedes spp. using the compound having the structure: ##STR1## This attractant finds utility primarily as a bait enhancer for acute toxins and/or trapping devices.

Dimethyl substituted oxymethyl cyclohexane derivatives and uses thereof

Described are substituted 2,6-dimethylbicyclo[3,3,1]- non-6-enes defined according to the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and wherein 'R' represents one of the moieties: ##STR2## processes for preparing same and uses thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, hair preparations, fabric softeners, fabric softener articles, cosmetic powders and perfumed polymers).

Substituted 2,6-dimethylbicyclo[3,3,1]non-6-enes, processes for

Described are substituted 2,6-dimethylbicyclo[3,3,1]-non-6-enes defined according to the generic structure: ##STR1## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and wherein 'R' represents one of the moieties: ##STR2## processes for preparing same and uses thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, hair preparations, fabric softeners, fabric softener articles, cosmetic powders and perfumed polymers).

Described are 2,6-dimethylbicyclo[3.3.1]non-6-ene-3-methanol and substituted derivatives thereof defined according to the generic structure: ##STR1## wherein each of the dashed lines represents a carbon-oxygen covalent bond or no bond; N is 0 or 1; R.sub.1 represents hydrogen, C.sub.1 -C.sub.2 lower alkyl, lower alkenyl, lower alkylenyl, C.sub.1 -C.sub.2 acyl, alkoxycarbonyl, magnesium halo or lithium; and R.sub.2 represents methyl or hydrogen as well as uses thereof (wherein R.sub.1 is not magnesium halo or lithium) for augmenting or enhancing the aroma of consumable materials selected from the group consisting of perfume compositions, perfumed articles, colognes, deodorizing articles, deodorizing compositions and malodor maskants.

2,6-dimethylbicyclo[3.3.1]non-6-ene-3-methanol, substituted derivatives

Described are p-methylenedioxyphenyl propionitrile and propiohydroxylamine derivatives defined according to the generic structure: ##STR1## wherein Z.sub.1 represents the moiety: ##STR2## and the moiety: ##STR3## and R.sub.1 is hydrogen or methyl and also having the generic structure: ##STR4## wherein X is HSO.sub.4.sup.-- ; SO.sub.4 ; .sup.= Cl.sup.-- ; Br.sup.-- ; PO.sub.4.sup..dbd. ; H.sub.2 PO.sub.4.sup.-- ; and HPO.sub.4.sup.= ; and the process of preparing these compounds.

p-methylenedioxyphenyl propionitrile derivatives, process for producing

Described are p-methylenedioxyphenyl propionitrile and propiohydroxylamine derivatives defined according to the generic structure: ##STR1## wherein Z.sub.1 represents the moiety: ##STR2## and the moiety: ##STR3## and R.sub.1 is hydrogen or methyl and also having the generic structure: ##STR4## wherein X is HSO.sub.3.sup.- ; SO.sub.4 ;=Cl.sup.- ; PO.sub.4.sup..tbd. ; H.sub.2 PO.sub.4.sup.- ; and HPO.sub.4.sup.=. The p-methylenedioxyphenyl propionitrile and propiohydroxylamine derivatives having the structures: ##STR5## have useful organoleptic properties in the perfumery area. Also described are processes for preparing such p-methylenedioxyphenyl propionitrile and propiohydroxylamine derivatives. The compounds defined according to the structure: ##STR6## are useful intermediates in such processes. The subgenus defined according to the structure: ##STR7## covers novel compounds.

P-methylenedioxyphenyl propionitrile derivatives, process for producing

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Hazlet, NJ, United States of America

Anubhav P Narula