# US 2014/0155261 A1 · Honeybee Repellents and Uses Thereof

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- Number: US 2014/0155261 A1
- Document ID: US20140155261A1
- Status: Published application
- Kind: A1
- Application number: 14/115,800
- Filed: 2012-05-04
- Published: 2014-06-05
- Earliest claimed: 2011-05-05
- Assignees: Inscent, Inc.
- Applicants: Inscent, Inc.
- Inventors: Daniel F. Woods; Spiros Dimitratos; Robin W. Justice
- Web page: https://patentgrep.com/patent/US20140155261A1

## CPC

- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 33/20: containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
- A01N 35/02: containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
- A01N 35/10: containing a carbon-to-nitrogen double bond
- A01N 37/10: Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
- A01N 37/28: containing the group [IMAGE cpc-sch-A01N-0937.gif]; Thio analogues thereof
- A01N 37/46: N-acyl derivatives
- A01N 43/10: with sulfur as the ring hetero atom
- A01N 43/12: condensed with a carbocyclic ring
- A01N 43/36: five-membered rings
- A01N 43/38: condensed with carbocyclic rings
- A01N 43/40: six-membered rings
- A01N 43/42: condensed with carbocyclic rings
- A01N 43/46: rings with more than six members
- A01N 43/60: 1,4-Diazines; Hydrogenated 1,4-diazines
- A01N 43/76: 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
- A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A01N 43/84: six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
- A01N 65/00: Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof (containing compounds of determined constitution A01N27/00 - A01N59/00)
- A01N 65/36: Rutaceae [Rue family], e.g. lime, orange, lemon, corktree or pricklyash
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

The present specification discloses honeybee repellents exhibiting repellent properties similar to 2-heptanone, compositions comprising such repellents, uses to repel a honeybee from a mammal, location, plant, structure treated of such repellents, and methods of treating a mammal, location, plant, structure by applying such repellents.

## Claims

### Claim at position 1

1-73. (canceled)

### Claim 74

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.

### Claim 75 (depends on 74)

The method of claim 74, wherein the honeybee repellent has a structure of formula I:
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;

### Claim 76 (depends on 74)

The method of claim 74, wherein the honeybee repellent has a structure of formula Ia:
wherein R3 and R4 are each independently H, C1-6 alkyl, OC1-6 alkyl, CO2C1-6 alkyl, phenoxymethanol, halogen, NO2, SO2 or when two of R3 or R4 are taken together form a cyclic group including, but not limited to, methylene dioxo, benzo, morpholino, piperidinyl, dioxanyl, pyranyl, optionally substituted heteroaryl, furanyl, thiophene, pyrrole, thiazole, isothiazole, imidazole, oxazole, isoxazole, pyridinyl, pyrimidinyl or piperazine; m is 0, 1 or 2; n is 0, 1 or 2; p is 0 to 5; and q is 0 to 5.

### Claim 77 (depends on 74)

The method of claim 74, wherein the honeybee repellent has a structure according to one of the following formulae:

### Claim 78 (depends on 74)

The method of claim 74, wherein the repelling a honeybee from a location or a structure or a plant prevents the honeybee from foraging and/or collecting nectar.

### Claim 79

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.

### Claim 80 (depends on 79)

The method of claim 79, wherein the honeybee repellent has a structure of formula I:
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;

### Claim 81 (depends on 79)

The method of claim 79, wherein the honeybee repellent has a structure of formula Ia:
wherein R3 and R4 are each independently H, C1-6 alkyl, OC1-6 alkyl, CO2C1-6 alkyl, phenoxymethanol, halogen, NO2, SO2 or when two of R3 or R4 are taken together form a cyclic group including, but not limited to, methylene dioxo, benzo, morpholino, piperidinyl, dioxanyl, pyranyl, optionally substituted heteroaryl, furanyl, thiophene, pyrrole, thiazole, isothiazole, imidazole, oxazole, isoxazole, pyridinyl, pyrimidinyl or piperazine; m is 0, 1 or 2; n is 0, 1 or 2; p is 0 to 5; and q is 0 to 5.

### Claim 82 (depends on 79)

The method of claim 79, wherein the honeybee repellent has a structure according to one of the following formulae:

### Claim 83 (depends on 79)

The seed composition of claim 79, wherein the composition further comprises one or more of an insecticide, a pesticide, a fungicide, a fertilizer of a micronutrient or macronutrient nature, a herbicide, a feeding inhibitor, an insect molting inhibitor, an insect mating inhibitor, an insect maturation inhibitor, a nematocide, a nutritional or horticultural supplement, a larvicide, a seed, or any combination thereof.

### Claim 84

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.

### Claim 85 (depends on 84)

The method of claim 84, wherein the honeybee repellent has a structure of formula I:
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;

### Claim 86 (depends on 84)

The method of claim 84, wherein the honeybee repellent has a structure of formula Ia:
wherein R3 and R4 are each independently H, C1-6 alkyl, OC1-6 alkyl, CO2C1-6 alkyl, phenoxymethanol, halogen, NO2, SO2 or when two of R3 or R4 are taken together form a cyclic group including, but not limited to, methylene dioxo, benzo, morpholino, piperidinyl, dioxanyl, pyranyl, optionally substituted heteroaryl, furanyl, thiophene, pyrrole, thiazole, isothiazole, imidazole, oxazole, isoxazole, pyridinyl, pyrimidinyl or piperazine; m is 0, 1 or 2; n is 0, 1 or 2; p is 0 to 5; and q is 0 to 5.

### Claim 87 (depends on 84)

The method of claim 84, wherein the honeybee repellent has a structure according to one of the following formulae: