Bedoukian Research, Inc.

Other

United States of America, As Represented by the Secretary of Agriculture

Biosensory, Inc.

Bedoukain Research, Inc.

Bedouklan Research, Inc.

Robert H Bedoukian

Daniel L Kline

Robert E Maloney

Patrick Foley

Hifzur R Ansari

James Nolen

Douglas Jay Pesak

Krzysztof Swierczek

James A Nolen

Linda C Passaro

Jim A Nolen

J A Nolen

Ashok Raina

Control or repellency of biting arthropods, particularly biting insects, is accomplished by bringing the biting arthropods into contact with combinations of compounds identical or related to those found on human/animal skin or in plants acting synergistically with one another, or in combination with conventional repellents like N,N-diethyl-3-methylbenzamide (DEET®), para-menthane-3,8-diol (PMD), sec-butyl-2-(2-hydroxyethyl) piperidine carboxylate ('Picaridin'), or other nitrogen containing repellents selected from amines, amides and nitrogen containing heterocyclic compounds, or any synergistic combination of DEET®, PMD, Picaridin, or other nitrogen containing repellents selected from amines, amides and nitrogen containing heterocyclic compounds.

Synergistic formulations for control and repellency of biting arthropods

This disclosure relates to a method for the control or repellency of biting arthropods. The method comprises bringing the biting arthropods into contact with a biting arthropod repellent formulation. The biting arthropod repellent formulation comprises nootkatone in combination, or in synergistic combination, with skin or plant derived compounds and compounds structurally similar to them (e.g., ketones, cyclic ketones, esters, gamma or delta lactones, and branched and/or unsaturated carboxylic acids), and/or one or more repellents selected from the group consisting of DEET&#xae;, para-menthane-3,8-diol (PMD), Picaridin, ethyl 3-[acetyl(butyl)amino]propanoate (IR3535), and other nitrogen-containing repellents including amines, amides, and nitrogen-containing heterocyclic compounds. This disclosure also relates to a biting arthropod repellent formulation comprising nootkatone in combination, or in synergistic combination, with the skin or plant derived compounds and compounds structurally similar to them, and/or the one or more repellents.

Synergistic biting arthropod repellent formulations

Compounds are used as agents that deter feeding by insect pests, such asand. Feeding deterrence is obtained by contact of the insect pests with at least one of the compounds of the structure (I) wherein R is &#x2014;OH, &#x2550;O, &#x2014;OC(O)R, &#x2014;OR, or &#x2014;(OR), each Ris independently an alkyl group containing from 1 to 4 carbon atoms and Ris 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 CHwith the proviso that when X is O, R can only be &#x2550;O; each Z is independently (CH) or (CH); y is a numeral selected from 1 and 2; Ris 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; Ris 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; Ris 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, &#x2014;(CH)OH, &#x2014;C(O)OR, &#x2014;CHC(O)OR, &#x2014;CHC(O)R, &#x2014;C(O)NRR, and &#x2014;CHC(O)NRRwhere each of R, R, R, R, R, Rand Ris 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; 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 9 to 20 total carbon atoms in the compounds.

Feeding deterrence of pests such asand

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) WhereinR is selected from &#x2014;OH, &#x2014;OC(O)R, &#x2014;OR, &#x2014;(OR), wherein each Ris independently selected from an alkyl group containing from 1 to 4 carbon atoms and Ris 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, with the proviso that when X is O, R can only be &#x2550;O;each Z is independently selected from (CH) and (CH)y is a numeral selected from 1 and 2;Ris 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.Ris 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.Ris 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, &#x2014;(CH)OH, &#x2014;C(O)OR, &#x2014;CHC(O)OR, &#x2014;CHC(O)R, &#x2014;C(O)NRR, &#x2014;CHC(O)NRRwhere each of R, R, R, R, R, Rand Ris 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; andthe 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 &#x2550;O, X&#x2550;CHand 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 &#x2550;O, X&#x2550;CHand 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 &#x2550;O, X&#x2550;CHand y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds.

Control and repellency of bed bugs

Formulations for control and repellency of biting arthropods

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) whereinR is &#x2014;OH, &#x2550;O, &#x2014;OC(O)R, &#x2014;OR, or &#x2014;(OR), wherein each Ris independently an alkyl group containing from 1 to 4 carbon atoms and Ris 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, with the proviso that when X is O R can only be &#x2550;O:each Z is independently (CH) or (CH);y is a numeral selected from 1 and 2;Ris 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;Ris 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;Ris H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, &#x2014;(CH)OH, &#x2014;C(O)OR, &#x2014;CHC(O)OR, &#x2014;CHC(O)R, &#x2014;C(O)NRR,or &#x2014;CHC(O)NRRwhere each of R, R, R, R, R, Rand Ris 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; andwherein the compounds of structure (I) contain from 11 to 20 carbon atoms except where R is &#x2550;O, X&#x2550;CHand y is 1 the compounds of structure (I) contain from 13 to 20 carbon atoms, with the proviso that when Ris &#x2014;CHC(O)ORRand Rmust 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

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); wherein R is selected from &#x2014;OH, &#x2014;OC(O)R, &#x2014;OR, &#x2014;(OR), wherein each Ris independently selected from an alkyl group containing from 1 to 4 carbon atoms and Ris 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, with the proviso that when X is O R can only be =0; each Z is independently selected from (CH) and (CH) y is a numeral selected from 1 and 2; Ris 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. Ris 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. Ris 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, &#x2014;(CH)OH, &#x2014;C(O)OR, &#x2014;CHC(O)OR, &#x2014;CHC(O)R, &#x2014;C(O)NRR, &#x2014;CHC(O)NRRwhere each of R, R, R, R, R, Rand Ris 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 () contain from 11 to 20 total carbon atoms, except where R is &#x2550;O, X&#x2550;CHand y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds, wherein the compounds of structure () contain from 11 to 20 total carbon atoms, except where R is &#x2550;O, X&#x2550;CH2 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 () contain from 11 to 20 total carbon atoms, except where R is =0, X&#x2550;CHand y is 1 the compounds of structure (I) contain from 13 to 20 total carbon atoms in the compounds. 

Killing one or more biting arthropods selected from the group consisting of mosquitoes, bed bugs and ticks is accomplished by bringing the biting arthropods into contact with a toxic amount of a formulation comprising: (1) one or more compounds of structure (I), wherein the compounds of structure (I) comprise: wherein R is selected from the group consisting of &#x2014;OH, &#x2550;O, &#x2014;OC(O)R, &#x2014;OR, &#x2014;(OR), wherein each Ris independently selected from an alkyl group containing from 1 to 4 carbon atoms and Ris 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, with the proviso that when X is O, then R can only be &#x2550;O; each Z is independently selected from the group consisting of (CH) and (CH); y is a numeral selected from 1 and 2; Ris selected from the group consisting of 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; Ris selected from the group consisting of 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; Ris selected from the group consisting of 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, &#x2014;(CH)OH, &#x2014;C(O)OR, &#x2014;CHC(O)OR, &#x2014;CHC(O)R, &#x2014;C(O)NRR, &#x2014;CHC(O)NRRwhere each of R, R, R, R, R, Rand Ris 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; 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 total carbon atoms; and (2) one or more toxicant compounds selected from the group consisting of pyrethroids, carbamates, and organophosphates. The formulation can be a synergistic formulation.

Formulations for killing biting arthropods

Killing one or more agricultural pests is accomplished by bringing the agricultural pests into contact with a toxic amount of a formulation comprising: (I) one or more compounds selected from the group consisting of: (1) one or more compounds of structure (A), wherein the compounds of structure (A) comprise: wherein R is selected from the group consisting of &#x2014;OH, &#x2550;O, &#x2014;OC(O)R, &#x2014;OR, &#x2014;(OR), wherein each Ris independently selected from an alkyl group containing from 1 to 4 carbon atoms and R 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, with the proviso that when X is O, then R can only be &#x2550;O; each Z is independently selected from the group consisting of (CH) and (CH); y is a numeral selected from 1 and 2; Ris selected from the group consisting of 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; Ris selected from the group consisting of 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; Ris selected from the group consisting of 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, &#x2014;(CH)OH, &#x2014;C(O)OR, &#x2014;CHC(O)OR, &#x2014;CHC(O)R, &#x2014;C(O)NRR, &#x2014;CHC(O)NRRwhere each of R, R, R, R, R, Rand Ris 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; 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 (A) contain from 11 to 20 total carbon atoms; and (2) one or more sesquiterpenes selected from the group consisting of acyclic, monocyclic, bicyclic and tricyclic sesquiterpenes and derivatives thereof; and (II) one or more toxicant compounds selected from the group consisting of carbamates, organochlorines, pyrethroids, sulfoximines, neonicotinoids, pyridine azomethines, diamides, organophosphates, phenylpyrazoles, oxadiazines, and ketoenols. The formulation can be a synergistic formulation.

Formulations for killing agricultural pests

This disclosure relates to a method for the control or repellency of biting arthropods. The method comprises bringing the biting arthropods into contact with a biting arthropod repellent formulation. The biting arthropod repellent formulation comprises an alkoxy nootkatol separate from, or in combination, or in synergistic combination, with skin or plant derived compounds and compounds structurally similar to them (e.g., ketones, cyclic ketones, esters, gamma or delta lactones, and branched and/or unsaturated carboxylic acids), and/or one or more repellents selected from the group consisting of DEET&#xae;, para-menthane-3,8-diol (PMD), Picaridin, ethyl 3-[acetyl(butyl)amino]propanoate (IR3535), and other nitrogen-containing repellents including amines, amides, and nitrogen-containing heterocyclic compounds. This disclosure also relates to a biting arthropod repellent formulation comprising an alkoxy nootkatol separate from, or in combination, or in synergistic combination, with the skin or plant derived compounds and compounds structurally similar to them, and/or the one or more repellents.

This disclosure relates to a method for the control or repellency of biting arthropods. The method comprises bringing the biting arthropods into contact with a biting arthropod repellent formulation. The biting arthropod repellent formulation comprises an alkoxy nootkatone separate from, or in combination, or in synergistic combination, with skin or plant derived compounds and compounds structurally similar to them (e.g., ketones, cyclic ketones, esters, gamma or delta lactones, and branched and/or unsaturated carboxylic acids), and/or one or more repellents selected from the group consisting of DEET&#xae;, para-menthane-3,8-diol (PMD), Picaridin, ethyl 3-[acetyl(butyl)amino]propanoate (IR3535), and other nitrogen-containing repellents including amines, amides, and nitrogen-containing heterocyclic compounds. This disclosure also relates to a biting arthropod repellent formulation comprising an alkoxy nootkatone separate from, or in combination, or in synergistic combination, with the skin or plant derived compounds and compounds structurally similar to them, and/or the one or more repellents.

Compounds are used as agents that deter feeding of crops by agricultural pests such as hemiptera, lepidoptera and coleoptera, including, but not limited to, stink bugs, codling moth larvae and granary weevils. Feeding deterrence is obtained by contact of the insects with at least one of the compounds of the structure (I) wherein R is &#x2014;OH, &#x2550;O, &#x2014;OC(O)R, &#x2014;OR, or &#x2014;(OR), wherein each R, is independently an alkyl group containing from 1 to 4 carbon atoms and Ris 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 CHwith the proviso that when X is OR can only be &#x2550;O; each Z is independently (CH) or (CH); y is a numeral selected from 1 and 2; Ris 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; Ris 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; Ris 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, &#x2014;(CH2)OH, &#x2014;C(O)OR, &#x2014;CHC(O)OR, &#x2014;CHC(O)R, &#x2014;C(O)NRR, and &#x2014;CHC(O)NRRwhere each of R, R, R, R, R, Rand Ris 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; 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 9 to 20 total carbon atoms in the compounds. 

Feeding deterrence in agricultural pests such as hemiptera, lepidoptera and coleoptera

A composition containing at least one isomeric alkoxynonenol, in particular, isomeric 8-alkoxy-4,8-dimethylnon-1-en-3-ol, in an amount effective to impart a fragrance to the composition. A fragrance composition containing at least one isomeric alkoxynonenol in an amount effective to impart a fragrance to the composition. A consumer product containing the fragrance composition having at least one isomeric alkoxynonenol in an amount effective to impart a fragrance to the composition. A method of imparting a fragrance to a consumer product by adding to the consumer product a fragrance composition containing at least one isomeric alkoxynonenol in an amount effective to impart a fragrance to the consumer product.

Fragrance compositions containing isomeric alkoxynonenols

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). 

A perfume composition comprising an effective amount of at least one alkadienenitrile selected from 4,8-undecadienenitrile and isomers thereof, 4,9-dodecadienenitrile and isomers thereof, and 4,10-tridecadienenitrile and isomers thereof. The isomers of 4,8-undecadienenitrile comprise Z,Z-4,8-undecadienenitrile, E,E-4,8-undecadienenitrile, and mixed Z/E isomers of 4,8-undecadienenitrile; the isomers of 4,9-dodecadienenitrile comprise Z,Z-4,9-dodecadienenitrile, E,E-4,9-dodecadienenitrile, and mixed Z/E isomers of 4,9-dodecadienenitrile; and the isomers of 4,10-tridecadienenitrile comprise Z,Z-4,10-tridecadienenitrile, E,E-4,10-tridecadienenitrile, and mixed Z/E isomers of 4,10-tridecadienenitrile. A composition comprising an effective amount of at least one alkadienenitrile selected from 4,8-undecadienenitrile and isomers thereof, 4,9-dodecadienenitrile and isomers thereof, and 4,10-tridecadienenitrile and isomers thereof. Processes for the preparation of the isomeric alkadienenitriles are provided. The isomeric alkadienenitriles have a range of fresh, citric, ozonic and floral notes of exceptional strength.

Growing community of inventors

West Redding, CT, United States of America

Robert H Bedoukian