Synergistic mixtures for arthropod toxicity and repellency

A composition comprising a compound of Formula II′ or a compound of Formula III′:

• where R6′ and R7′ are each independently selected from the group consisting of hydrogen, halo, haloalkyl, C6-C12 heteroaryl, haloaryl, C6-C12 aryl, alkenyl, alkynyl, and C1-C3 alkyl;
• or
• wherein R6′ and R7′ are taken together with the carbon to which they are attached to form a C6-C12 heteroaryl, C6-C12 aryl, C3-C12 cycloalkyl, haloaryl, or C3-C12 heterocycloalkyl;
• R8′ and R9′ are each independently selected from hydrogen haloalkyl, alkenyl, alkynyl, and C1-C6 alkyl;
• X″ is selected from the group consisting of O, NH, and S;
• R21′, R22′, R23′, R24′, and R25′ are each independently selected from the group consisting of hydrogen, alkoxy, halo, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, and C1-C3 alkyl-alkoxy;
• P′ is selected from the group consisting of O, NH, and S;
• R26′ is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl;
• and
• a compound selected from the group consisting of an essential oil, a pyrethroid, methyl jasmonate, IR3535, 2-undecanone, picaridin, benzaldehyde, p-menthane-3,8-diol, alpha-terpineyl isovalerate, DEET, benzyl benzoate, ethyl hexanediol, diethyl phthalate, diethyl carbate, geraniol, nootkatone, citronellol, citronellal, citral, oil of lemon eucalyptus, cinnamaldehyde, and VUAA-1,
• wherein the composition is synergistic, in admixture with a carrier.

A composition comprising a compound of Formula IV, a compound of Formula V, or a compound of Formula VI:

• wherein Y is selected from the group consisting of O, NH, and S;
• R11 is selected from the group consisting of hydrogen, C1-C6 alkyl, alkenyl, alkynyl, CN, halo, and haloalkyl;
• R19 and R20 are each independently selected from the group consisting of hydrogen, C1-C6 alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, arylalkyl, heterocycloalkyl, heteroarylalkyl, halo, and alkoxy, wherein said cycloalkyl, cycloalkylalkyl, arylalkyl, heterocycloalkyl, or heteroarylalkyl is optionally substituted with C1-C6 alkyl;
• or
• where the substituents on R19 and R20, taken together with the carbon to which each is attached, form a C5-C7 cycloalkyl;
• X1, X2, and X3 are each independently selected from the group consisting of CH, CH2, O, S, N, C═O, and NH;
• and
• wherein at least one of X1, X2, and X3 is substituted with —COH;
• R13, R14, R15, R16, and R17 are each independently selected from the group consisting of hydrogen, alkoxy, halo, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, and C1-C3 alkyl-alkoxy;
• R18 is selected from the group consisting of hydrogen, haloalkyl, and linear or branched C1-C6 alkyl;
• and
• a compound of Formula II′ or a compound of Formula III′:
• wherein R6′ and R7′ are each independently selected from the group consisting of hydrogen, halo, haloalkyl, C6-C12 heteroaryl, haloaryl, C6-C12 aryl, alkenyl, alkynyl, and C1-C3 alkyl;
• or
• wherein R6′ and R7′ are taken together with the carbon to which they are attached to form a C6-C12 heteroaryl, C6-C12 aryl, C3-C12 cycloalkyl, haloaryl, or C3-C12 heterocycloalkyl;
• R8′ and R9′ are each independently selected from hydrogen and C1-C6 alkyl;
• X″ is selected from the group consisting of O, NH, and S;
• R21′, R22′, R23′, R24′, and R25′ are each independently selected from the group consisting of hydrogen, alkoxy, halo, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, and C1-C3 alkyl-alkoxy;
• P′ is selected from the group consisting of O, NH, and S;
• R26′ is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl,
• wherein the composition is synergistic, in admixture with a carrier.

A composition comprising a compound of Formula VII

• wherein R28 is selected from the group consisting of hydrogen, haloalkyl, alkoxy, alkenyl, alkynyl, and C1-C6 linear or branched alkyl;
• R30, R31, R32, R33, and R34 are each independently selected from the group consisting of hydrogen, linear or branched C1-C6 alkyl, alkoxy, halo, cyano, haloalkyl, alkenyl, alkynyl, hydroxy, and
• wherein M is selected from the group consisting of O, NH, and S;
• R40, R41, R42, R43, and R44 are each independently selected from the group consisting of hydrogen, linear or branched C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, halo, cyano, hydroxy;
• and
• a compound selected from the group consisting of an essential oil, a pyrethroid, methyl jasmonate, IR3535, 2-undecanone, picaridin, benzaldehyde, p-menthane-3,8-diol, alpha-terpineyl isovalerate, nootkatone, DEET, VUAA-1, a compound of Formula II′, a compound of Formula III′, a compound of Formula IV, a compound of Formula V, and a compound of Formula VI
• wherein R6′ and R7′ are each independently selected from the group consisting of hydrogen, halo, haloalkyl, C6-C12 heteroaryl, haloaryl, C6-C12 aryl, alkenyl, alkynyl, and C1-C3 alkyl;
• or
• wherein R6′ and R7′ are taken together with the carbon to which they are attached to form a C6-C12 heteroaryl, C6-C12 aryl, C3-C12 cycloalkyl, haloaryl, or C3-C12 heterocycloalkyl;
• R8′ and R9′ are each independently selected from hydrogen haloalkyl, alkenyl, alkynyl, and C1-C6 alkyl;
• X″ is selected from the group consisting of O, NH, and S;
• R21′, R22′, R23′, R24′, and R25′ are each independently selected from the group consisting of hydrogen, alkoxy, halo, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, and C1-C3 alkyl-alkoxy;
• P′ is selected from the group consisting of O, NH, and S;
• R26′ is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl;
• Y is selected from the group consisting of O, NH, and S;
• R11 is selected from the group consisting of hydrogen, C1-C6 alkyl, alkenyl, alkynyl, CN, halo, and haloalkyl;
• R19 and R20 are each independently selected from the group consisting of hydrogen, C1-C6 alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, arylalkyl, heterocycloalkyl, heteroarylalkyl, halo, and alkoxy, wherein said cycloalkyl, cycloalkylalkyl, arylalkyl, heterocycloalkyl, or heteroarylalkyl is optionally substituted with C1-C6 alkyl;
• or
• where the substituents on R19 and R20, taken together with the carbon to which each is attached, form a C5-C7 cycloalkyl;
• X1, X2, and X3 are each independently selected from the group consisting of CH, CH2, O, S, N, C═O, and NH;
• and
• wherein at least one of X1, X2, and X3 is substituted with —COH;
• R13, R14, R15, R16, and R17 are each independently selected from the group consisting of hydrogen, alkoxy, halo, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, and C1-C3 alkyl-alkoxy;
• R18 is selected from the group consisting of hydrogen, alkenyl, alkynyl, haloalkyl, and linear or branched C1-C6 alkyl,
• wherein the composition is synergistic, in admixture with a carrier.

A composition comprising a compound of Formula I′, and a compound of Formula II′ or a compound of Formula III′

• wherein R1′ and R2′ are each independently selected from the group consisting of hydrogen, halo, haloalkyl, C6-C12 heteroaryl, haloaryl, C6-C12 aryl, alkenyl, alkynyl, and C1-C3 alkyl;
• or
• wherein R1′ and R2′ are taken together with the carbon to which they are attached to form a C6-C12 heteroaryl, C6-C12 aryl, C3-C12 cycloalkyl, haloaryl, or C3-C12 heterocycloalkyl;
• R3′ and R4′ are each independently selected from hydrogen, haloalkyl, alkenyl, alkynyl, and C1-C6 alkyl;
• R5′ is selected from the group consisting of linear or branched C1-C12 alkyl, haloalkyl, alkenyl, alkynyl, C3-C12 cycloalkyl, C3-C12 cycloalkylalkyl, C6-C12 aryl, C6-C12 arylalkyl, C6-C12 heteroaryl, and C3-C12 heterocycloalkyl;
• X′ is selected from the group consisting of O, NH, and S;
• R6′ and R7′ are each independently selected from the group consisting of hydrogen, halo, haloalkyl, C6-C12 heteroaryl, haloaryl, C6-C12 aryl, alkenyl, alkynyl, and C1-C3 alkyl;
• or
• wherein R1′ and R2′ are taken together with the carbon to which they are attached to form a C6-C12 heteroaryl, C6-C12 aryl, C3-C12 cycloalkyl, haloaryl, or C3-C12 heterocycloalkyl;
• R8′ and R9′ are each independently selected from hydrogen, haloalkyl, alkenyl, alkynyl, and C1-C6 alkyl;
• X″ is selected from the group consisting of O, NH, and S;
• R21′, R22′, R23′, R24′, and R25′ are each independently selected from the group consisting of hydrogen, alkoxy, halo, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, and C1-C3 alkyl-alkoxy;
• P′ is selected from the group consisting of O, NH, and S;
• R26′ is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl, and
• wherein the composition is synergistic, in admixture with a carrier.

A method of repelling an arthropod from an object or locus, comprising contacting said object or locus with a composition comprising a compound of Formula II′ or a compound of Formula III′:

• wherein R6′ and R7′ are each independently selected from the group consisting of hydrogen, halo, haloalkyl, C6-C12 heteroaryl, haloaryl, C6-C12 aryl, alkenyl, alkynyl, and C1-C3 alkyl;
• or
• wherein R6′ and R7′ are taken together with the carbon to which they are attached to form a C6-C12 heteroaryl, C6-C12 aryl, C3-C12 cycloalkyl, haloaryl, or C3-C12 heterocycloalkyl;
• R8′ and R9′ are each independently selected from hydrogen, haloalkyl, alkenyl, alkynyl, and C1-C6 alkyl;
• X″ is selected from the group consisting of O, NH, and S;
• R21′, R22′, R23′, R24′, and R25′ are each independently selected from the group consisting of hydrogen, alkoxy, halo, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, and C1-C3 alkyl-alkoxy;
• P′ is selected from the group consisting of O, NH, and S;
• R26′ is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl;
• and
• a compound selected from the group consisting of an essential oil, a pyrethroid, methyl jasmonate, IR3535, 2-undecanone, picaridin, benzaldehyde, p-menthane-3,8-diol, alpha-terpineyl isovalerate, nootkatone, DEET, benzyl benzoate, ethyl hexanediol, diethyl phthalate, diethyl carbate, geraniol, citronellol, citronellal, citral, oil of lemon eucalyptus, cinnamaldehyde, and VUAA-1,
• wherein the composition is synergistic, in admixture with a carrier.

A method of repelling an arthropod from an object or locus, comprising contacting said object or locus with a composition comprising a compound of Formula IV, a compound of Formula V, or a compound of Formula VI

• wherein Y is selected from the group consisting of O, NH, and S;
• R11 is selected from the group consisting of hydrogen, C1-C6 alkyl, alkenyl, alkynyl, CN, halo, and haloalkyl;
• R19 and R20 are each independently selected from the group consisting of hydrogen, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, arylalkyl, heterocycloalkyl, heteroarylalkyl, halo, and alkoxy, wherein said cycloalkyl, cycloalkylalkyl, arylalkyl, heterocycloalkyl, or heteroarylalkyl is optionally substituted with C1-C6 alkyl;
• or
• where the substituents on R19 and R20, taken together with the carbon to which each is attached, form a C5-C7 cycloalkyl;
• X1, X2, and X3 are each independently selected from the group consisting of CH, CH2, O, S, N, C═O, and NH;
• and
• wherein at least one of X1, X2, and X3 is substituted with —COH;
• R13, R14, R15, R16, and R17 are each independently selected from the group consisting of hydrogen, alkoxy, halo, haloalkyl, alkenyl, alkynyl, C1-C6 alkyl, and C1-C3 alkyl-alkoxy;
• R18 is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl;
• and
• a compound of Formula II′ or a compound of Formula III′
• R6′ and R7′ are each independently selected from the group consisting of hydrogen, halo, haloalkyl, C6-C12 heteroaryl, haloaryl, C6-C12 aryl, alkenyl, alkynyl, and C1-C3 alkyl;
• or
• wherein R6′ and R7′ are taken together with the carbon to which they are attached to form a C6-C12 heteroaryl, C6-C12 aryl, C3-C12 cycloalkyl, haloaryl, or C3-C12 heterocycloalkyl;
• R8′ and R9′ are each independently selected from hydrogen, haloalkyl, alkenyl, alkynyl, and C1-C6 alkyl;
• X″ is selected from the group consisting of O, NH, and S;
• R21′, R22′, R23′, R24′, and R25′ are each independently selected from the group consisting of hydrogen, alkoxy, halo, haloalkyl, alkenyl, alkynyl, C1-C6 alkyl, and C1-C3 alkyl-alkoxy;
• P′ is selected from the group consisting of O, NH, and S;
• R26′ is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl,
• wherein the composition is synergistic, in admixture with a carrier.

A method of repelling an arthropod from an object or locus, comprising contacting said object or locus with a composition comprising a compound of Formula VII

• wherein R28 is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, alkoxy, and C1-C6 linear or branched alkyl;
• R30, R31, R32, R33, and R34 are each independently selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, linear or branched C1-C6 alkyl, alkoxy, halo, cyano, hydroxy, and
• wherein M is selected from the group consisting of O, NH, and S;
• R40, R41, R42, R43, and R44 are each independently selected from the group consisting of hydrogen, linear or branched C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, halo, cyano, hydroxy;
• and
• a compound selected from the group consisting of an essential oil, a pyrethroid, methyl jasmonate, IR3535, 2-undecanone, picaridin, benzaldehyde, p-menthane-3,8-diol, alpha-terpineyl isovalerate, DEET, VUAA-1, nootkatone, a compound of Formula II′, a compound of Formula III′, a compound of Formula IV, a compound of Formula V, and a compound of Formula VI
• wherein R6′ and R7′ are each independently selected from the group consisting of hydrogen, halo, haloalkyl, C6-C12 heteroaryl, haloaryl, C6-C12 aryl, alkenyl, alkynyl, and C1-C3 alkyl;
• or
• wherein R6′ and R7′ are taken together with the carbon to which they are attached to form a C6-C12 heteroaryl, C6-C12 aryl, C3-C12 cycloalkyl, haloaryl, or C3-C12 heterocycloalkyl;
• R8′ and R9′ are each independently selected from hydrogen, haloalkyl, alkenyl, alkynyl, and C1-C6 alkyl;
• X″ is selected from the group consisting of O, NH, and S;
• R21′, R22′, R23′, R24′, and R25′ are each independently selected from the group consisting of hydrogen, alkoxy, halo, haloalkyl, alkenyl, alkynyl, C1-C6 alkyl, and C1-C3 alkyl-alkoxy;
• P′ is selected from the group consisting of O, NH, and S;
• R26′ is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl;
• Y is selected from the group consisting of O, NH, and S;
• R11 is selected from the group consisting of hydrogen, alkenyl, alkynyl, C1-C6 alkyl, CN, halo, and haloalkyl;
• R19 and R20 are each independently selected from the group consisting of hydrogen, C1-C6 alkyl, cycloalkylalkyl, arylalkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, heteroarylalkyl, halo, and alkoxy, wherein said cycloalkyl, cycloalkylalkyl, arylalkyl, heterocycloalkyl, or heteroarylalkyl is optionally substituted with C1-C6 alkyl;
• or
• where the substituents on R19 and R20, taken together with the carbon to which each is attached, form a C5-C7 cycloalkyl;
• X1, X2, and X3 are each independently selected from the group consisting of CH, CH2, O, S, N, C═O, and NH;
• and
• wherein at least one of X1, X2, and X3 is substituted with —COH;
• R13, R14, R15, R16, and R17 are each independently selected from the group consisting of hydrogen, alkoxy, haloalkyl, alkenyl, alkynyl, halo, C1-C6 alkyl, and C1-C3 alkyl-alkoxy;
• R18 is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl,
• wherein the composition is synergistic, in admixture with a carrier.

A method of repelling an arthropod from an object or locus, comprising contacting said object or locus with a composition comprising a compound of Formula I′

• and a compound of Formula II′ or a compound of Formula III′
• wherein R1′ and R2′ are each independently selected from the group consisting of hydrogen, halo, haloalkyl, C6-C12 heteroaryl, haloaryl, C6-C12 aryl, alkenyl, alkynyl, and C1-C3 alkyl;
• or
• wherein R6′ and R7′ are taken together with the carbon to which they are attached to form a C6-C12 heteroaryl, C6-C12 aryl, C3-C12 cycloalkyl, haloaryl, or C3-C12 heterocycloalkyl;
• R3′ and R4′ are each independently selected from hydrogen, haloalkyl, alkenyl, alkynyl, and C1-C6 alkyl;
• R5′ is selected from the group consisting of linear or branched C1-C12 alkyl, haloalkyl, alkenyl, alkynyl, C3-C12 cycloalkyl, C3-C12 cycloalkylalkyl, C6-C12 aryl, C6-C12 arylalkyl, C6-C12 heteroaryl, and C3-C12 heterocycloalkyl;
• X′ is selected from the group consisting of O, NH, and S;
• R6′ and R7′ are each independently selected from the group consisting of hydrogen, halo, haloalkyl, C6-C12 heteroaryl, haloaryl, C6-C12 aryl, alkenyl, alkynyl, and C1-C3 alkyl;
• or
• wherein R8′ and R9′ are taken together with the carbon to which they are attached to form a C6-C12 heteroaryl, C6-C12 aryl, C3-C12 cycloalkyl, haloaryl, or C3-C12 heterocycloalkyl;
• R8′ and R9′ are each independently selected from hydrogen, haloalkyl, alkenyl, alkynyl, and C1-C6 alkyl;
• X″ is selected from the group consisting of O, NH, and S;
• R21′, R22′, R23′, R24′, and R25′ are each independently selected from the group consisting of hydrogen, alkoxy, halo, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, and C1-C3 alkyl-alkoxy;
• P′ is selected from the group consisting of O, NH, and S;
• R26′ is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl,
• wherein the composition is synergistic, in admixture with a carrier.

A method for controlling one or more arthropods, comprising exposing said one or more arthropods to a synergistic composition comprising a compound of Formula II′ or a compound of Formula III′:

• wherein R6′ and R7′ are each independently selected from the group consisting of hydrogen, halo, haloalkyl, C6-C12 heteroaryl, haloaryl, C6-C12 aryl, alkenyl, alkynyl, and C1-C3 alkyl;
• or
• wherein R6′ and R7′ are taken together with the carbon to which they are attached to form a C6-C12 heteroaryl, C6-C12 aryl, C3-C12 cycloalkyl, or C3-C12 heterocycloalkyl;
• R8′ and R9′ are each independently selected from hydrogen, haloalkyl, alkenyl, alkynyl, and C1-C6 alkyl;
• X″ is selected from the group consisting of O, NH, and S;
• R21′, R22′, R23′, R24′, and R25′ are each independently selected from the group consisting of hydrogen, alkoxy, halo, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, and C1-C3 alkyl-alkoxy;
• P′ is selected from the group consisting of O, NH, and S;
• R26′ is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl;
• and
• a pyrethroid,
• wherein the synergistic composition produces, when the one or more arthropods are exposed to the synergistic composition, a combined toxicant effect greater than the sum of the separate toxicant effects from the compound of Formula II′ or Formula III′ and the pyrethroid, at comparable concentrations.

A method of repelling an arthropod from an object or locus, comprising contacting said object or locus with a composition comprising a carrier and a compound of Formula II, Formula III, Formula IV, Formula V, Formula VI, or Formula VII

• wherein R6 and R7 are each independently selected from the group consisting of hydrogen, halo, haloalkyl, C6-C2 heteroaryl, haloaryl, C6-C12 aryl, alkenyl, alkynyl, and C1-C3 alkyl;
• or
• wherein R6′ and R7′ are taken together with the carbon to which they are attached to form a C6-C12 heteroaryl, C6-C12 aryl, C3-C12 cycloalkyl, haloaryl, or C3-C12 heterocycloalkyl;
• R8 and R9 are each independently selected from hydrogen, haloalkyl, alkenyl, alkynyl, and C1-C6 alkyl;
• R10 is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, linear or branched C1-C12 alkyl, C3-C12 cycloalkyl, C3-C12 cycloalkylalkyl, C6-C12 aryl, C6-C12 arylalkyl, C6-C12 heteroaryl, and C3-C12 heterocycloalkyl;
• X is selected from the group consisting of O, NH, and S;
• R21, R22, R23, R24, and R25 are each independently selected from the group consisting of hydrogen, alkoxy, halo, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, and C1-C3 alkyl-alkoxy;
• P is selected from the group consisting of O, NH, and S;
• R26 is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl;
• R27 is selected from the group consisting of hydrogen, linear or branched C1-C12 alkyl, haloalkyl, alkenyl, alkynyl, C3-C12 cycloalkyl, C3-C12 cycloalkylalkyl, C6-C12 aryl, C6-C12 arylalkyl, C6-C12 heteroaryl, and C3-C12 heterocycloalkyl;
• R11 is selected from the group consisting of hydrogen, C1-C6 alkyl, alkenyl, alkynyl, CN, halo, and haloalkyl;
• R19 and R20 are each independently selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, C1-C6 alkyl, cycloalkyl, cycloalkylalkyl, arylalkyl, heterocycloalkyl, heteroarylalkyl, halo, and alkoxy, wherein said cycloalkyl, cycloalkylalkyl, arylalkyl, heterocycloalkyl, or heteroarylalkyl is optionally substituted with C1-C6 alkyl;
• or
• where the substituents on R19 and R20, taken together with the carbon to which each is attached, form a C5-C7 cycloalkyl;
• X1, X2, and X3 are each independently selected from the group consisting of CH, CH2, O, S, N, C═O, and NH;
• and
• wherein at least one of X1, X2, and X3 is substituted with —COH;
• R13, R14, R15, R16, and R17 are each independently selected from the group consisting of hydrogen, alkoxy, halo, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, and C1-C3 alkyl-alkoxy;
• R18 is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl;
• R28 is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, alkoxy, and C1-C6 linear or branched alkyl;
• R30, R31, R32, R33, and R34 are each independently selected from the group consisting of hydrogen, linear or branched C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, halo, cyano, hydroxy, and
• wherein M is selected from the group consisting of O, NH, and S;
• and
• R40, R41, R42, R43, and R44 are each independently selected from the group consisting of hydrogen, linear or branched C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, halo, cyano, hydroxy.

A composition comprising an essential oil;

• and a second compound selected from the group consisting of a pyrethroid, a compound of Formula II, Formula III, Formula IV, Formula V, Formula VI, and Formula VII
• wherein R6 and R7 are each independently selected from the group consisting of hydrogen, halo, haloalkyl, C6-C2 heteroaryl, haloaryl, C6-C12 aryl, alkenyl, alkynyl, and C1-C3 alkyl;
• or
• wherein R6′ and R7′ are taken together with the carbon to which they are attached to form a C6-C2 heteroaryl, C6-C12 aryl, C3-C12 cycloalkyl, haloaryl, or C3-C12 heterocycloalkyl;
• R8 and R9 are each independently selected from hydrogen haloalkyl, alkenyl, alkynyl, and C1-C6 alkyl;
• R10 is selected from the group consisting of hydrogen, linear or branched C1-C12 alkyl, haloalkyl, alkenyl, alkynyl, C3-C12 cycloalkyl, C3-C12 cycloalkylalkyl, C6-C12 aryl, C6-C12 arylalkyl, C6-C12 heteroaryl, and C3-C12 heterocycloalkyl;
• X is selected from the group consisting of O, NH, and S;
• R21, R22, R23, R24, and R25 are each independently selected from the group consisting of hydrogen, alkoxy, halo, haloalkyl, alkenyl, alkynyl, C1-C6 alkyl, and C1-C3 alkyl-alkoxy;
• P is selected from the group consisting of O, NH, and S;
• R26 is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl;
• R27 is selected from the group consisting of hydrogen, linear or branched C1-C12 alkyl, haloalkyl, alkenyl, alkynyl, C3-C12 cycloalkyl, C3-C12 cycloalkylalkyl, C6-C12 aryl, C6-C12 arylalkyl, C6-C12 heteroaryl, and C3-C12 heterocycloalkyl;
• R11 is selected from the group consisting of hydrogen, C1-C6 alkyl, alkenyl, alkynyl, CN, halo, and haloalkyl;
• R19 and R20 are each independently selected from the group consisting of hydrogen, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, arylalkyl, heterocycloalkyl, heteroarylalkyl, halo, and alkoxy, wherein said cycloalkyl, cycloalkylalkyl, arylalkyl, heterocycloalkyl, or heteroarylalkyl is optionally substituted with C1-C6 alkyl;
• or
• where the substituents on R19 and R20, taken together with the carbon to which each is attached, form a C5-C7 cycloalkyl;
• X1, X2, and X3 are each independently selected from the group consisting of CH, CH2, O, S, N, C═O, and NH;
• and
• wherein at least one of X1, X2, and X3 is substituted with —COH;
• R13, R14, R15, R16, and R17 are each independently selected from the group consisting of hydrogen, alkoxy, halo, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, and C1-C3 alkyl-alkoxy;
• R18 is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl;
• R28 is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, alkoxy, and C1-C6 linear or branched alkyl;
• R30, R31, R32, R33, and R34 are each independently selected from the group consisting of hydrogen, linear or branched C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, halo, cyano, hydroxy, and
• wherein M is selected from the group consisting of O, NH, and S;
• R40, R41, R42, R43, and R44 are each independently selected from the group consisting of hydrogen, linear or branched C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, halo, cyano, hydroxy,
• wherein the composition is synergistic, in admixture with a carrier.

A method of repelling an arthropod from an object or locus, comprising contacting said object or locus with a composition comprising an essential oil, and a second compound selected from the group consisting of a pyrethroid, a compound of Formula II, Formula III, Formula IV, Formula V, Formula VI, and Formula VII

• wherein R6 and R7 are each independently selected from the group consisting of hydrogen, halo, haloalkyl, C6-C12 heteroaryl, haloaryl, C6-C12 aryl, alkenyl, alkynyl, and C1-C3 alkyl;
• or
• wherein R6′ and R7′ are taken together with the carbon to which they are attached to form a C6-C12 heteroaryl, C6-C12 aryl, C3-C12 cycloalkyl, haloaryl, or C3-C12 heterocycloalkyl;
• R8 and R9 are each independently selected from hydrogen haloalkyl, alkenyl, alkynyl, and C1-C6 alkyl;
• R10 is selected from the group consisting of hydrogen, linear or branched C1-C12 alkyl, C3-C12 cycloalkyl, haloalkyl, alkenyl, alkynyl, C3-C12 cycloalkylalkyl, C6-C12 aryl, C6-C12 arylalkyl, C6-C12 heteroaryl, and C3-C12 heterocycloalkyl;
• X is selected from the group consisting of O, NH, and S;
• R21, R22, R23, R24, and R25 are each independently selected from the group consisting of hydrogen, alkoxy, halo, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, and C1-C3 alkyl-alkoxy;
• P is selected from the group consisting of O, NH, and S;
• R26 is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl;
• R27 is selected from the group consisting of hydrogen, linear or branched C1-C12 alkyl, C3-C12 cycloalkyl, haloalkyl, alkenyl, alkynyl, C3-C12 cycloalkylalkyl, C6-C12 aryl, C6-C12 arylalkyl, C6-C12 heteroaryl, and C3-C12 heterocycloalkyl;
• R11 is selected from the group consisting of hydrogen, C1-C6 alkyl, alkenyl, alkynyl, CN, halo, and haloalkyl;
• R19 and R20 are each independently selected from the group consisting of hydrogen, C1-C6 alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, arylalkyl, heterocycloalkyl, heteroarylalkyl, halo, and alkoxy, wherein said cycloalkyl, cycloalkylalkyl, arylalkyl, heterocycloalkyl, or heteroarylalkyl is optionally substituted with C1-C6 alkyl;
• or
• where the substituents on R19 and R20, taken together with the carbon to which each is attached, form a C5-C7 cycloalkyl;
• X1, X2, and X3 are each independently selected from the group consisting of CH, CH2, O, S, N, C═O, and NH;
• and
• wherein at least one of X1, X2, and X3 is substituted with —COH;
• R13, R14, R15, R16, and R17 are each independently selected from the group consisting of hydrogen, alkoxy, halo, C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, and C1-C3 alkyl-alkoxy;
• R18 is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, and linear or branched C1-C6 alkyl;
• R28 is selected from the group consisting of hydrogen, haloalkyl, alkenyl, alkynyl, alkoxy, and C1-C6 linear or branched alkyl;
• R30, R31, R32, R33, and R34 are each independently selected from the group consisting of hydrogen, linear or branched C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, halo, cyano, hydroxy, and
• wherein M is selected from the group consisting of O, NH, and S;
• R40, R41, R42, R43, and R44 are each independently selected from the group consisting of hydrogen, linear or branched C1-C6 alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, halo, cyano, hydroxy,
• wherein the composition is synergistic, in admixture with a carrier.