Honeybee Repellents and Uses Thereof

A method of repelling a honeybee from a location or a structure or a plant, the method comprising the step of applying a honeybee to the location, the structure, the plant and/or in a vicinity nearby the location, the structure, or the plant, wherein application of the honeybee repellent to the location, the structure or the plant repels a honeybee from the location, the structure, or the plant, wherein the honeybee repellent has a repellent activity that substantially mimics a repellent chemosensory cue of 2-heptanone, and wherein the honeybee repellent has a structure of one of the following formulae:

• wherein X1 and X2 are each independently selected from CH, N and O;
• R1 and R2 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted aryl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted cyclic heteroalkyl, optionally substituted cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, or isoquinoline, with the proviso that if X1 is O, then R1 is not present, or if X2 is O, then R2 is not present;
• wherein X is O or S;
• Y is H, C1-6 alkyl, optionally substituted aryl, ═O, or ═S;
• Z1, Z2, and Z3 are each independently selected from N, NH, C, CH, CH2, O, or S;
• each R1 is independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted benzylidine, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, isoquinoline or when two of R1 are taken together form an optionally substituted cyclic group including, but not limited to, methylene dioxo, benzo, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophene, pyrrole, thiazole, isothiazole, imidazole, oxazole, isoxazole, pyridinyl, pyrimidinyl or piperazine;
• if Z1 is O or S, then R2 is absent, otherwise R2 is H, OH, C1-6 alkyl, optionally substituted aryl;
• a dashed line represents the presence or absence of a double bond;
• and m is 0 to 2;
• wherein X1 is O, N or S;
• R1 and R2 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted aryl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, or isoquinoline;
• m is 0 to 5;
• and n is 0 to 5;
• wherein X2 is O, N or S;
• R3 and R4 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, C═N—OH, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, or isoquinoline;
• o is 0 to 5;
• and p is 0 to 5;
• wherein X3 is O, NH or S;
• A1 and A2 are each independently selected from optionally substituted phenyl, optionally substituted morpholino, optionally substituted piperidinyl, optionally substituted dioxanyl, optionally substituted pyranyl, optionally substituted heteroaryl, optionally substituted furanyl, optionally substituted thiophenyl, optionally substituted tetrazole, optionally substituted thiazole, optionally substituted isothiazole, optionally substituted imidazole, optionally substituted thiadiazole, optionally substituted thiadiazole S-oxide, optionally substituted thiadiazole optionally substituted S,S-dioxide, optionally substituted sulfonylamidine, optionally substituted sulfonylguanidine, optionally substituted sulfamoylamidine, optionally substituted sulfamoylguanidine, optionally substituted pyrazole, optionally substituted oxazole, optionally substituted isoxazole, optionally substituted pyridinyl, optionally substituted pyrimidinyl, optionally substituted piperazine, optionally substituted quinoline, optionally substituted dihydroquinoline, and optionally substituted isoquinoline;
• and r is 0 to 5;
• wherein R7, R8 and R9 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• u is 0 to 5;
• v is 0 to 5;
• and w is 0 to 5;
• wherein each R10 is independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted phenyl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• and x is 0 to 9;
• wherein R11 and R12 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• the dashed line represents the presence or absence of a double bond;
• y is 0 to 9;
• and z is 0 to 5;
• wherein R is H, OH, halogen, C1-6 alkyl;
• R13 and R14 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• Y1 and Y2 are each independently selected from O, S, NH, or CH2;
• Z is O or S;
• a is 0 to 5;
• and b is 0 to 9;
• wherein each R15 is independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• and c is 0 to 5;
• wherein each R16 is independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• and d is 0 to 9;
• wherein R17 and R18 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• a dashed line represent the presence or absence of a double bond;
• e is 0 to 5;
• and f is 0 to 5;
• or
• wherein X1 and X2 are each independently selected from O, N or S;
• and R1, R2, R3, and R4 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, optionally substituted benzoyl, optionally substituted 2-benzoylethenyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, optionally substituted heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, isoquinoline or when R3 and R4 are taken together form a cyclic group including, but not limited to, methylene dioxo, benzo, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophene, pyrrole, thiazole, isothiazole, imidazole, oxazole, isoxazole, pyridinyl, pyrimidinyl or piperazine and substituted derivatives thereof.

A seed composition comprising a seed and a honeybee repellent, wherein the honeybee repellent has a repellent activity that substantially mimics a repellent chemosensory cue of 2-heptanone, and wherein the honeybee repellent has a structure of one of the following formulae:

• wherein X1 and X2 are each independently selected from CH, N and O;
• R1 and R2 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted aryl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted cyclic heteroalkyl, optionally substituted cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, or isoquinoline, with the proviso that if X1 is O, then R1 is not present, or if X2 is O, then R2 is not present;
• wherein X is O or S;
• Y is H, C1-6 alkyl, optionally substituted aryl, ═O, or ═S;
• Z1, Z2, and Z3 are each independently selected from N, NH, C, CH, CH2, O, or S;
• each R1 is independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted benzylidine, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, isoquinoline or when two of R1 are taken together form an optionally substituted cyclic group including, but not limited to, methylene dioxo, benzo, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophene, pyrrole, thiazole, isothiazole, imidazole, oxazole, isoxazole, pyridinyl, pyrimidinyl or piperazine;
• if Z1 is O or S, then R2 is absent, otherwise R2 is H, OH, C1-6 alkyl, optionally substituted aryl;
• a dashed line represents the presence or absence of a double bond;
• and m is 0 to 2;
• wherein X1 is O, N or S;
• R1 and R2 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted aryl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, or isoquinoline;
• m is 0 to 5;
• and n is 0 to 5;
• wherein X2 is O, N or S;
• R3 and R4 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, C═N—OH, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, or isoquinoline;
• o is 0 to 5;
• and p is 0 to 5;
• wherein X3 is O, NH or S;
• A1 and A2 are each independently selected from optionally substituted phenyl, optionally substituted morpholino, optionally substituted piperidinyl, optionally substituted dioxanyl, optionally substituted pyranyl, optionally substituted heteroaryl, optionally substituted furanyl, optionally substituted thiophenyl, optionally substituted tetrazole, optionally substituted thiazole, optionally substituted isothiazole, optionally substituted imidazole, optionally substituted thiadiazole, optionally substituted thiadiazole S-oxide, optionally substituted thiadiazole optionally substituted S,S-dioxide, optionally substituted sulfonylamidine, optionally substituted sulfonylguanidine, optionally substituted sulfamoylamidine, optionally substituted sulfamoylguanidine, optionally substituted pyrazole, optionally substituted oxazole, optionally substituted isoxazole, optionally substituted pyridinyl, optionally substituted pyrimidinyl, optionally substituted piperazine, optionally substituted quinoline, optionally substituted dihydroquinoline, and optionally substituted isoquinoline;
• and r is 0 to 5;
• wherein R7, R8 and R9 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• u is 0 to 5;
• v is 0 to 5;
• and w is 0 to 5;
• wherein each R10 is independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted phenyl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• and x is 0 to 9;
• wherein R11 and R12 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• the dashed line represents the presence or absence of a double bond;
• y is 0 to 9;
• and z is 0 to 5;
• wherein R is H, OH, halogen, C1-6 alkyl;
• R13 and R14 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• Y1 and Y2 are each independently selected from O, S, NH, or CH2;
• Z is O or S;
• a is 0 to 5;
• and b is 0 to 9;
• wherein each R15 is independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• and c is 0 to 5;
• wherein each R16 is independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• and d is 0 to 9;
• wherein R17 and R18 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• a dashed line represent the presence or absence of a double bond;
• e is 0 to 5;
• and f is 0 to 5;
• or
• wherein X1 and X2 are each independently selected from O, N or S;
• and R1, R2, R3, and R4 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, optionally substituted benzoyl, optionally substituted 2-benzoylethenyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, optionally substituted heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, isoquinoline or when R3 and R4 are taken together form a cyclic group including, but not limited to, methylene dioxo, benzo, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophene, pyrrole, thiazole, isothiazole, imidazole, oxazole, isoxazole, pyridinyl, pyrimidinyl or piperazine and substituted derivatives thereof.

A device comprising a honeybee repellent, wherein the honeybee repellent substantially mimics a repellent chemosensory cue of 2-heptanone, and wherein the honeybee repellent has a structure of one of the following formulae:

• wherein X1 and X2 are each independently selected from CH, N and O;
• R1 and R2 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted aryl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted cyclic heteroalkyl, optionally substituted cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, or isoquinoline, with the proviso that if X1 is O, then R1 is not present, or if X2 is O, then R2 is not present;
• wherein X is O or S;
• Y is H, C1-6 alkyl, optionally substituted aryl, ═O, or ═S;
• Z1, Z2, and Z3 are each independently selected from N, NH, C, CH, CH2, O, or S;
• each R1 is independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted benzylidine, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, isoquinoline or when two of R1 are taken together form an optionally substituted cyclic group including, but not limited to, methylene dioxo, benzo, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophene, pyrrole, thiazole, isothiazole, imidazole, oxazole, isoxazole, pyridinyl, pyrimidinyl or piperazine;
• if Z1 is O or S, then R2 is absent, otherwise R2 is H, OH, C1-6 alkyl, optionally substituted aryl;
• a dashed line represents the presence or absence of a double bond;
• and m is 0 to 2;
• wherein X1 is O, N or S;
• R1 and R2 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted aryl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, or isoquinoline;
• m is 0 to 5;
• and n is 0 to 5;
• wherein X2 is O, N or S;
• R3 and R4 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, C═N—OH, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, or isoquinoline;
• o is 0 to 5;
• and p is 0 to 5;
• wherein X3 is O, NH or S;
• A1 and A2 are each independently selected from optionally substituted phenyl, optionally substituted morpholino, optionally substituted piperidinyl, optionally substituted dioxanyl, optionally substituted pyranyl, optionally substituted heteroaryl, optionally substituted furanyl, optionally substituted thiophenyl, optionally substituted tetrazole, optionally substituted thiazole, optionally substituted isothiazole, optionally substituted imidazole, optionally substituted thiadiazole, optionally substituted thiadiazole S-oxide, optionally substituted thiadiazole optionally substituted S,S-dioxide, optionally substituted sulfonylamidine, optionally substituted sulfonylguanidine, optionally substituted sulfamoylamidine, optionally substituted sulfamoylguanidine, optionally substituted pyrazole, optionally substituted oxazole, optionally substituted isoxazole, optionally substituted pyridinyl, optionally substituted pyrimidinyl, optionally substituted piperazine, optionally substituted quinoline, optionally substituted dihydroquinoline, and optionally substituted isoquinoline;
• and r is 0 to 5;
• wherein R7, Wand R9 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• u is 0 to 5;
• v is 0 to 5;
• and w is 0 to 5;
• wherein each R10 is independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted phenyl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• and x is 0 to 9;
• wherein R11 and R12 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• the dashed line represents the presence or absence of a double bond;
• y is 0 to 9;
• and z is 0 to 5;
• wherein R is H, OH, halogen, C1-6 alkyl;
• R13 and R14 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• Y1 and Y2 are each independently selected from O, S, NH, or CH2;
• Z is O or S;
• a is 0 to 5;
• and b is 0 to 9;
• wherein each R15 is independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• and c is 0 to 5;
• wherein each R16 is independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• and d is 0 to 9;
• wherein R17 and R18 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, ═S, ═O, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino;
• a dashed line represent the presence or absence of a double bond;
• e is 0 to 5;
• and f is 0 to 5;
• or
• wherein X1 and X2 are each independently selected from O, N or S;
• and R1, R2, R3, and R4 are each independently selected from H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, optionally substituted alkylaryl, optionally substituted arylalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted alkoxyalkylaryl, alkylamino, aminoalkyl, dialkylamino, optionally substituted arylamino, optionally substituted aminoaryl, heteroalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, cyclic heteroalkyl, cyclic heteroalkylalkyl, acyl, optionally substituted benzoyl, optionally substituted 2-benzoylethenyl, NH2, NR5R6, OH, OR5, CN, NO2, OCF3, CF3, Br, Cl, F, 1-amidino, 2-amidino, alkylcarbonyl, morpholino, piperidinyl, dioxanyl, pyranyl, optionally substituted heteroaryl, furanyl, thiophenyl, tetrazole, thiazole, isothiazole, imidazole, thiadiazole, thiadiazole S-oxide, thiadiazole S,S-dioxide, sulfonylamidine, sulfonylguanidine, sulfamoylamidine, sulfamoylguanidine, pyrazole, oxazole, isoxazole, pyridinyl, pyrimidinyl, piperazine, quinoline, isoquinoline or when R3 and R4 are taken together form a cyclic group including, but not limited to, methylene dioxo, benzo, morpholino, piperidinyl, dioxanyl, pyranyl, heteroaryl, furanyl, thiophene, pyrrole, thiazole, isothiazole, imidazole, oxazole, isoxazole, pyridinyl, pyrimidinyl or piperazine and substituted derivatives thereof.