Compounds for pest control and methods for their use
AssigneeThe United States of America as represented by the Department of Health and Human Services
InventorsGary O. Maupin, Joseph Karchesy, Nicholas A. Panella, Marc C. Dolan
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Abstract
Compounds, compositions, and methods that employ an eremophilane sesguiterpene are presented for controlling an arthropod pest population. The compounds have minimal adverse or toxic effects on humans, non-human animals, and the natural environment. The compounds may be isolated from natural sources, semi-synthesized from naturally occurring compounds, or completely synthesized. The compounds may be applied directly to a pest or the locus of a pest, and function as topical or ingestible toxins. Eremophilane sesguiterpenes 13-hydroxy-valencene, valencene-11,12-epoxide, valencene-13-aldehyde, and nootkatone-1,10-11,12-diepoxide are exemplary compounds.
Claims47
A compound, other than valencene, nootkatone, nootkatol, epinootkatol, or nootkatene, having the formula:
- where Y is
- R1, R2, and R12 are each independently selected from lower aliphatic, lower aliphatic hydroxy, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy;
- R1′ is selected from lower aliphatic other than methyl, lower aliphatic hydroxy, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy;
- R3, R4, R5, R6, R7, R8, and R11 are each independently selected from H, ═O, —OH, lower aliphatic, lower aliphatic hydroxy, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy;
- R9 and R10 are each lower aliphatic;
- and
- R1, R2, R3, R4, R5, R6, R7, R8 R9 R10 R11, and R12 satisfy valence requirements.
A compound, other than valencene, nootkatone, nootkatol, epinootkatol, or nootkatene, comprising a compound selected from the group consisting of:
- a compound having the formula:
- a compound having the formula:
- a compound having the formula:
- a compound having the formula:
- and a compound having the formula:
- wherein Y1 is
- Y2 is
- Y3 is
- R1, R2, and R8 are each independently selected from lower aliphatic, lower aliphatic hydroxy, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy;
- R1′ is lower aliphatic, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy;
- R3, R4, R5, R6, and R7 are each independently selected from H, ═O, —OH, lower aliphatic, lower aliphatic hydroxy, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy;
- R5′ is H, —OH, lower aliphatic, lower aliphatic hydroxy lonwer aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy;
- and
- R1, R2, R3, R4, R5, R6, R7, and R8 satisfy valence requirements.
A pesticidal composition, the composition comprising:
- (a) a pesticidally effective amount of a compound other than nootkatone or valencene having the formula:
- where Y is
- R1, R3, R4, R7, R8, and R11 are each independently selected from H, ═O, —OH, lower aliphatic, lower aliphatic hydroxy, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy;
- R2, and R12 are each independently selected from ═O, —OH, lower aliphatic, lower aliphatic hydroxy, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy;
- and
- R5, and R6 are each independently selected from H, ═O, —OH, lower aliphatic, lower aliphatic hydroxy, lower aliphatic sulfydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy, or together are:
- R9, and R10 are each independently selected from lower aliphatic, lower alipahtic hydroxy, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy;
- and
- R1, R2, R3, R4, R5, R6, R7, R8 R9 R10 R11, and R12 satisfy valence requirements;
- and
- (b) a pesticidally acceptable carrier, additive or adjuvant.
A method for controlling an arthropod, comprising contacting an arthropod with a pesticidally effective amount of a compound other than nootkatone or valencene having the formula:
- where Y is
- R1, R3, R4, R7, R8, and R11 are each independently seleeted form H, ═O, —OH, lower aliphatic, lower aliphatic hydroxy, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic, ether, or lower aliphatic epoxy;
- R2, and R12 are each independently selected front ═O, —OH, lower aliphatic, lower aliphatic hydroxy, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbornyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy, radical;
- and
- R5, and R6 are each independently selected from H, ═O, —OH, lower aliphatic, lower aliphatic hydroxy, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy, or together are:
- R9, and R10 are each independently selected from lower aliphatic, lower aliphatic hydroxy, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy;
- and
- R1, R2, R3, R4, R5, R6, R7, R8 R9 R10 R11, and R12 satisfy valence requirements.
A method for controlling an arthropod, comprising contacting an arthropod with a pesticidally effective amount of a compound other than nootkatone or valencene selected from the group consisting of:
- a compound having the formula:
- a compound having the formula:
- a compound having the formula:
- and a compound having the formula:
- wherein Y is
- R1, R3, R4, R5, R6, and R7 are each independently selected from H, ═O, —OH, lower aliphatic, lower aliphatic hydroxy, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy;
- R2 and R8 are each independently selected from ═O, —OH, lower aliphatic, lower aliphatic hydroxy, lower aliphatic sulfhydryl, carbonyl-containing lower aliphatic, thiocarbonyl-containing lower aliphatic, lower aliphatic ether, or lower aliphatic epoxy;
- and
- R1, R2, R3, R4, R5, R6, R7, and R8 satisfy valence requirements.
Dependencies are inferred from the claim text.