Control or repellency of bed bugs is accomplished by bringing the bed bugs into contact with at least one of the compounds of the structure (I) ##STR00001##
Wherein
R is selected from —OH, —OC(O)R.sub.4, —OR.sub.6, —(OR.sub.6).sub.2, wherein each R.sub.6 is independently selected from an alkyl group containing from 1 to 4 carbon atoms and R.sub.4 is a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
X is O or CH.sub.2, with the proviso that when X is O, R can only be ═O;
each Z is independently selected from (CH) and (CH.sub.2)
y is a numeral selected from 1 and 2;
R.sub.1 is selected from H or a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms.
R.sub.2 is selected from H and a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms.
R.sub.3 is selected from H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, —(CH.sub.2).sub.nOH, —C(O)OR.sub.5, —CH.sub.2C(O)OR.sub.7, —CH.sub.2C(O)R.sub.8, —C(O)NR.sub.9R.sub.10, —CH.sub.2C(O)NR.sub.11R.sub.12 where each of R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 is independently selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, and n is an integer of from 1 to 12; and
the bond between the 2 and 3 positions in the ring structure may be a single or a double bond, and wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds. wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds. wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds.

Control or repellency of bed bugs is accomplished by bringing the bed bugs into contact with at least one of the compounds of the structure (I) ##STR00001##
Wherein
R is selected from —OH, —OC(O)R.sub.4, —OR.sub.6, —(OR.sub.6).sub.2, wherein each R.sub.6 is independently selected from an alkyl group containing from 1 to 4 carbon atoms and R.sub.4 is a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
X is O or CH.sub.2, with the proviso that when X is O, R can only be ═O;
each Z is independently selected from (CH) and (CH.sub.2)
y is a numeral selected from 1 and 2;
R.sub.1 is selected from H or a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms.
R.sub.2 is selected from H and a branched or straight chain saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms.
R.sub.3 is selected from H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, —(CH.sub.2).sub.nOH, —C(O)OR.sub.5, —CH.sub.2C(O)OR.sub.7, —CH.sub.2C(O)R.sub.8, —C(O)NR.sub.9R.sub.10, —CH.sub.2C(O)NR.sub.11R.sub.12 where each of R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 is independently selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, and n is an integer of from 1 to 12; and
the bond between the 2 and 3 positions in the ring structure may be a single or a double bond, and wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds. wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds. wherein the compounds of structure (1) contain from 11 to 20 total carbon atoms, except where R is ═O, X═CH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds.

The invention discloses a process for the oxidation of limonene, comprising the reaction of limonene with hydrogen peroxide in the presence of a catalyst containing atoms and/or ions of at least one metal, selected from the group consisting of molybdenum, tungsten, scandium, vanadium, titanium, lanthanum, zirconium, praseodymium, neodymium, samarium, europium, terbium, dysprosium, erbium or ytterbium, characterised in that the molecular weight of the catalyst is less than 2,000 g/mol and that the reaction is performed at a pH value of more than 7.5.

The invention discloses a process for the oxidation of limonene, comprising the reaction of limonene with hydrogen peroxide in the presence of a catalyst containing atoms and/or ions of at least one metal, selected from the group consisting of molybdenum, tungsten, scandium, vanadium, titanium, lanthanum, zirconium, praseodymium, neodymium, samarium, europium, terbium, dysprosium, erbium or ytterbium, characterised in that the molecular weight of the catalyst is less than 2,000 g/mol and that the reaction is performed at a pH value of more than 7.5.

The present invention refers to 6-isopropyl-2,4-dimethylcyclohexen-1-ol derivatives, to a method of their production, and fragrance compositions and fragranced articles comprising them.

The present invention refers to 6-isopropyl-2,4-dimethylcyclohexen-1-ol derivatives, to a method of their production, and fragrance compositions and fragranced articles comprising them.

Control and repellency of biting flies, house flies, ticks, ants, fleas, biting midges, cockroaches, spiders and stink bugs is obtained by contact of the insects with at least one of the compounds of the structure (I) ##STR00001##
wherein
R is OH, O, OC(O)R.sub.4, OR.sub.6, or (OR.sub.6).sub.2, wherein each R.sub.6 is independently an alkyl group containing from 1 to 4 carbon atoms and R.sub.4 is a branched or straight chain, saturated or unsaturated, hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
X is O or CH.sub.2, with the proviso that when X is O R can only be O:
each Z is independently (CH) or (CH.sub.2);
y is a numeral selected from 1 and 2;
R.sub.1 is H or a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
R.sub.2 is H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms;
R.sub.3 is H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, (CH.sub.2).sub.nOH, C(O)OR.sub.5, CH.sub.2C(O)OR.sub.7, CH.sub.2C(O)R.sub.8, C(O)NR.sub.9R.sub.10,
or CH.sub.2C(O)NR.sub.11R.sub.12 where each of R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 is independently H or a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, and n is n integer of from 1 to 12;
the bond between the 2 and 3 positions in the ring structure may be a single or a double bond; and
wherein the compounds of structure (I) contain from 11 to 20 carbon atoms except where R is O, XCH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 carbon atoms, with the proviso that when R.sub.3 is CH.sub.2C(O)OR.sub.7 R.sub.1 and R.sub.2 must be H or a saturated hydrocarbyl group with zero double bonds. The invention also includes optical isomers, diastereomers and enantiomers of the compounds of structure (I).

Control and repellency of biting flies, house flies, ticks, ants, fleas, biting midges, cockroaches, spiders and stink bugs is obtained by contact of the insects with at least one of the compounds of the structure (I) ##STR00001##
wherein
R is OH, O, OC(O)R.sub.4, OR.sub.6, or (OR.sub.6).sub.2, wherein each R.sub.6 is independently an alkyl group containing from 1 to 4 carbon atoms and R.sub.4 is a branched or straight chain, saturated or unsaturated, hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
X is O or CH.sub.2, with the proviso that when X is O R can only be O:
each Z is independently (CH) or (CH.sub.2);
y is a numeral selected from 1 and 2;
R.sub.1 is H or a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms;
R.sub.2 is H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms;
R.sub.3 is H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, (CH.sub.2).sub.nOH, C(O)OR.sub.5, CH.sub.2C(O)OR.sub.7, CH.sub.2C(O)R.sub.8, C(O)NR.sub.9R.sub.10,
or CH.sub.2C(O)NR.sub.11R.sub.12 where each of R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 is independently H or a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, and n is n integer of from 1 to 12;
the bond between the 2 and 3 positions in the ring structure may be a single or a double bond; and
wherein the compounds of structure (I) contain from 11 to 20 carbon atoms except where R is O, XCH.sub.2 and y is 1 the compounds of structure (I) contain from 13 to 20 carbon atoms, with the proviso that when R.sub.3 is CH.sub.2C(O)OR.sub.7 R.sub.1 and R.sub.2 must be H or a saturated hydrocarbyl group with zero double bonds. The invention also includes optical isomers, diastereomers and enantiomers of the compounds of structure (I).

A process for purifying a crude composition includes a monoterpene compound selected from the group consisting of monocyclic monoterpene alcohols, monocyclic monoterpene ketones, bicyclic epoxy monoterpenes and mixtures of two or more of the aforementioned compounds, such as preferably a monocyclic monoterpene alcohol. The process comprises performing a layer crystallization with a melt of the crude composition, and the melt of the crude composition subjected to the layer crystallization includes oxygen-containing solvent in a concentration of 20 ppm to 2% by weight. The oxygen-containing solvent is selected from the group consisting of water, C1-6-alcohols, C1-6-carboxylic acids, C1-6-ketones, C1-6-aldehydes, C1-12-ethers, C1-12-esters and mixtures of two or more of the aforementioned solvents.

A process for purifying a crude composition includes a monoterpene compound selected from the group consisting of monocyclic monoterpene alcohols, monocyclic monoterpene ketones, bicyclic epoxy monoterpenes and mixtures of two or more of the aforementioned compounds, such as preferably a monocyclic monoterpene alcohol. The process comprises performing a layer crystallization with a melt of the crude composition, and the melt of the crude composition subjected to the layer crystallization includes oxygen-containing solvent in a concentration of 20 ppm to 2% by weight. The oxygen-containing solvent is selected from the group consisting of water, C1-6-alcohols, C1-6-carboxylic acids, C1-6-ketones, C1-6-aldehydes, C1-12-ethers, C1-12-esters and mixtures of two or more of the aforementioned solvents.