Control of resistant pests

Abstract

Methods of controlling pesticide resistant pests include exposing the pesticide resistant pests to a pest controlling amount of a triketone compound. Formulations and kits can include the triketone compound.

What is claimed is: 
     
         1 . A method of controlling pesticide resistant pests comprising exposing the pesticide resistant pests to a compound of formula (I) 
       
         
           
           
               
               
           
         
         wherein:
 R 1  is selected from the group consisting of —C(═O)R 7 , —OR 8 , —SR 8 , -C 1-10 hydroxyalkyl, —NR 9 R 10 , —C(═N—R 9 )R 7 , —C(═N—OH)R 7 , —NO, —NO 2 , —N(OR 8 )R 7  and —OSO 3 R 8 ; 
 R 2  is selected from the group consisting of hydrogen, -C 1-10 alkyl, -C 2-10 alkenyl, aryl and heteroaryl; 
 R 3 , R 4 , R 5  and R 6  are each independently selected from the group consisting of hydrogen, -C 1-10 alkyl, -C 3-6 cycloalkyl, -C 2-10 alkenyl, -C 1-10 haloalkyl, -C 1-10 dihaloalkyl, -C 1-10 trihaloalkyl, —OR 8 , —SR 8 , —NR 9 R 10 , —C(═N—R 9 )R 7 , —NO, —NO 2 , —NR 9 OR 8 , —OSO 3 R 8 , -C 1-10 alkylaryl and —C(═O)R 7 ; 
 R 7  is selected from the group consisting of hydrogen, -C 1-10 alkyl, -C 2-10 alkylaryl, C 3-6 cycloalkyl, -C 2-10 alkenyl, -C 1-10 alkylheteroaryl, -C 1-10 haloalkyl, -C 1-10 dihaloalkyl, -C 1-10 trihaloalkyl, -C 1-10 haloalkoxy, -C 1-10 hydroxyalkyl, -C 1-10 thioalkyl, -C 1-10 nitroalkyl, -C 1-3 alkylOC 1-3 alkyl, -C 1-3 alkylOC 1-3 haloalkyl, -C 1-3 alkylOC 1-3 dihaloalkyl, -C 1-3 alkylOC 1-3 trihaloalkyl, —OR 8 , —SR 8  and —NR 9 R 10 ; 
 R 8  is selected from the group consisting of hydrogen, -C 1-10 alkyl, -C 2-10 alkylaryl, -C 3-6 cycloalkyl, -C 2-10 alkenyl, -C 1-10 alkylheteroaryl, -C 1-10 haloalkyl, -C 1-10 dihaloalkyl, -C 1-10 trihaloalkyl, -C 1-10 haloalkoxy, -C 1-10 hydroxyalkyl, -C 1-10 thioalkyl and -C 1-10 nitroalkyl; 
 R 9  and R 10  are independently selected from the group consisting of hydrogen, -C 1-10 alkyl, -C 2-10 alkylaryl, -C 3-6 cycloalkyl, -C 2-10 alkenyl, -C 1-10 alkylheteroaryl, -C 1-10 haloalkyl, -C 1-10 dihaloalkyl, -C 1-10 trihaloalkyl; or a tautomer thereof. 
 
       
     
     
         2 . The method according to  claim 1  wherein the compound of formula (I) is a compound of formula (II): 
       
         
           
           
               
               
           
         
         wherein:
 R 11  is selected from —CR 12 R 13 R 14  or —NR 15 R 1   6 ; 
 one of R 12  and R 13  is hydrogen and the other is hydroxyl or —OCR 17 R 18 R 19  or R 12  and R 13  together form an oxo group (═O) or a ═N—OH group; 
 R 14  is —CH(CH 3 )CR 20 R 21 R 22 , —CH 2 CH(CH 3 )CR 20 R 21 R 22  or —CH(CH 3 )CH 2 CR 20 R 21 R 22 ; 
 R 15  and R 16  are independently selected from the group consisting of hydrogen and C 1-10 alkyl; 
 R 17 , R 18  and R 19  are independently selected from hydrogen or halo; and 
 R 20 , R 21  and R 22  are independently selected from the group consisting of hydrogen, hydroxyl, halo, NO 2  and —OCR 17 R 18 R 9 ; or a tautomer thereof. 
 
       
     
     
         3 . The method according to  claim 1  wherein the compound of formula (I) is a compound of formula (III): 
       
         
           
           
               
               
           
         
         wherein:
 one of R 23  and R 24  is hydrogen and the other is hydroxyl or —OCR 27 R 28 R 29  or R 23  and R 24  together form an oxo group (═O); 
 R 25  is —CR 30 R 31 R 32 , —CH 2 CR 30 R 31 R 32  or —CH(CH 3 )CR 30 R 31 R 32 ; 
 R 26  is H or —CH 3 ; wherein where R 26  is H, R 25  is —CH(CH 3 )CR 30 R 31 R 32 ; 
 R 27 , R 28  and R 29  are independently selected from hydrogen or halo; and 
 R 30 , R 31  and R 32  are independently selected from the group consisting of hydrogen, hydroxyl, halo, NO 2  and —OCR 27 R 28 R 29 ; or a tautomer thereof. 
 
       
     
     
         4 . The method according to  claim 1  wherein the compound of formula (I) is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       or a tautomer thereof. 
     
     
         5 . The method according to  claim 1 , wherein the compound of formula (I) is selected from the group consisting of flavesone, leptospermone and isoleptospermone. 
     
     
         6 . The method according to  claim 5  wherein the compound of formula (I) is flavesone. 
     
     
         7 . The method according to  claim 1 , wherein the pesticide resistant pests are insects resistant to one or more insecticides or arachnids resistant to one or more arachnicides. 
     
     
         8 . The method according to  claim 7  wherein the arachnid is an acarina (tick or mite). 
     
     
         9 . The method according to  claim 8  wherein the acarina is cattle tick or cattle tick larvae. 
     
     
         10 . The method according to  claim 1 , wherein the pesticide resistant pest is exposed to the compounds of formula (I) in an amount in the range of about 200 ppm to about 800 ppm or about 300 ppm to about 600 ppm, or about 300 ppm to about 600 ppm or about 800 ppm to about 2,500 ppm or about 900 ppm to about 2000 ppm. 
     
     
         11 . The method according to  claim 7  wherein the insect is selected from the group consisting of  Rhyzopertha dominica, Sitophilus oryzae, Triobolium castaneum, Oryzaephilus surinamensis  or  Cryptolestes ferrugineus.    
     
     
         12 . The method according to  claim 11  wherein the insect is an adult. 
     
     
         13 . The method according to  claim 7  wherein the arachnid is selected from the group consisting of  Halotydeus destructor, Penthaleus  spp,  Balaustium medicagoense  and  Bryobia mite.    
     
     
         14 . The method according to  claim 13  wherein the arachnid is infesting a crop. 
     
     
         15 . The method according to  claim 1 , wherein a pesticide resistant pest is exposed to a compound of formula (I) in combination with a second pesticide. 
     
     
         16 . The method according to  claim 15  wherein the second pesticide has a different mode of action from the compound of formula (I). 
     
     
         17 . The method according to  claim 15  wherein the second pesticide is selected from the group consisting of at least one of a sodium channel modulator, an acetylcholinesterase (AChE) inhibitor, a GABA-gated chloride channel antagonist, a nicotinergic acetylcholine receptor agonist, an allosteric acetylcholine receptor modulator, a chloride channel actuator, a juvenile hormone mimic, a homopteran feeding blocker, a mitochondrial ATP synthase inhibitor, an uncoupler of oxidative phosphorylation, a nicotinic acetylcholine receptor channel blocker, an inhibitor of chitin biosynthesis, a moulting disruptor, an ecdysone receptor agonist or disruptor, an octapamine receptor agonist, a mitochondrial complex I electron transport inhibitor, an acetyl CoA carboxylase inhibitor, a voltage-dependent sodium channel blocker, a mitochondrial complex IV electron inhibitor, a mitochondrial complex IV electron transport inhibitor and a ryanodine receptor modulator. 
     
     
         18 . A method of treating or preventing a pest infestation in a livestock animal or a companion animal comprising applying to the animal an effective amount of a compound of formula (I): 
       
         
           
           
               
               
           
         
         wherein:
 R 1  is selected from the group consisting of —C(═O)R 7 , —OR 8 , —SR 8 , -C 1-10 hydroxyalkyl, —NR 9 R 10 , —C(═N—R 9 )R 7 , —C(═N—OH)R 7 , —NO, —NO 2 , —N(OR 8 )R 7  and —OSO 3 R 8 ; 
 R 2  is selected from the group consisting of hydrogen, -C 1-10 alkyl, -C 2-10 alkenyl, aryl and heteroaryl; 
 R 3 , R 4 , R 5  and R 6  are each independently selected from the group consisting of hydrogen, -C 1-10 alkyl, -C 3-6 cycloalkyl, -C 2-10 alkenyl, -C 1-10 haloalkyl, -C 1-10 dihaloalkyl, -C 1-10 trihaloalkyl, —OR 8 , —SR 8 , —NR 9 R 10 , —C(═N—R 9 )R 7 , —NO, —NO 2 , —NR 9 OR 8 , —OSO 3 R 8 , -C 1-10 alkylaryl and —C(═O)R 7 ; 
 R 7  is selected from the group consisting of hydrogen, -C 1-10 alkyl, -C 2-10 alkylaryl, C 3-6 cycloalkyl, -C 2-10 alkenyl, -C 1-10 alkylheteroaryl, -C 1-10 haloalkyl, -C 1-10 dihaloalkyl, -C 1-10 trihaloalkyl, -C 1-10 haloalkoxy, -C 1-10 hydroxyalkyl, -C 1-10 thioalkyl, -C 1-10 nitroalkyl, -C 1-3 alkylOC 1-3 alkyl, -C 1-3 alkylOC 1-3 haloalkyl, -C 1-3 alkylOC 1-3 dihaloalkyl, -C 1-3 alkylOC 1-3 trihaloalkyl, —OR 8 , —SR 8  and —NR 9 R 10 ; 
 R 8  is selected from the group consisting of hydrogen, -C 1-10 alkyl, -C 2-10 alkylaryl, -C 3-6 cycloalkyl, -C 2-10 alkenyl, -C 1-10 alkylheteroaryl, -C 1-10 haloalkyl, -C 1-10 dihaloalkyl, -C 1-10 trihaloalkyl, -C 1-10 haloalkoxy, -C 1-10 hydroxyalkyl, -C 1-10 thioalkyl and -C 1-10 nitroalkyl; 
 R 9  and R 10  are independently selected from the group consisting of hydrogen, -C 1-10 ioalkyl, -C 2-10 alkylaryl, -C 3-6 cycloalkyl, -C 2-10 alkenyl, -C 1-10 alkylheteroaryl, -C 1-10 haloalkyl, -C 1-10 dihaloalkyl, and -C 1-10 trihaloalkyl; or a tautomer thereof; 
 
         wherein the pest infestation is caused by a population of pests comprising pesticide resistant pests. 
       
     
     
         19 . A method of  claim 1 , wherein the pests are a population of pests, wherein the population of pests comprises pesticide resistant pests. 
     
     
         20 . A method of protecting stored plant parts from pest infestation comprising contacting the plant part with a compound of formula (I) 
       
         
           
           
               
               
           
         
         wherein:
 R 1  is selected from the group consisting of —C(═O)R 7 , —OR 8 , —SR 8 , -C 1-10 hydroxyalkyl, —NR 9 R 10 , —C(═N—R 9 )R 7 , —C(═N—OH)R 7 , —NO, —NO 2 , —N(OR 8 )R 7  and —OSO 3 R 8 ; 
 R 2  is selected from the group consisting of hydrogen, -C 1-10 alkyl, -C 2-10 alkenyl, aryl and heteroaryl; 
 R 3 , R 4 , R 5  and R 6  are each independently selected from the group consisting of hydrogen, -C 1-10 alkyl, -C 3-6 cycloalkyl, -C 2-10 alkenyl, -C 1-10 haloalkyl, -C 1-10 dihaloalkyl, -C 1-10 trihaloalkyl, —OR 8 , —SR 8 , —NR 9 R 10 , —C(═N—R 9 )R 7 , —NO, —NO 2 , —NR 9 OR 8 , —OSP 3 R 8 , -C 1-10 alkylaryl and —C(═O)R 7 ; 
 R 7  is selected from the group consisting of hydrogen, -C 1-10 alkyl, -C 2-10 alkylaryl, C 3-6 cycloalkyl, -C 2-10 alkenyl, -C 1-10 alkylheteroaryl, -C 1-10 haloalkyl, -C 1-10 dihaloalkyl, -C 1-10 trihaloalkyl, -C 1-10 haloalkoxy, -C 1-10 hydroxyalkyl, -C 1-10 thioalkyl, -C 1-10 nitroalkyl, -C 1-3 alkylOC 1-3 alkyl, -C 1-3 alkylOC 1-3 haloalkyl, -C 1-3 alkylOC 1-3 dihaloalkyl, -C 1-3 alkylOC 1-3 trihaloalkyl, —OR 8 , —SR 8  and —NR 9 R 10 ; 
 R 8  is selected from the group consisting of hydrogen, -C 1-10 alkyl, -C 2-10 alkylaryl, -C 3-6 cycloalkyl, -C 2-10 alkenyl, -C 1-10 alkylheteroaryl, -C 1-10 haloalkyl, -C 1-10 dihaloalkyl, -C 1-10 trihaloalkyl, -C 1-10 haloalkoxy, -C 1-10 hydroxyalkyl, -C 1-10 thioalkyl and -C 1-10 nitroalkyl; 
 R 9  and R 10  are independently selected from the group consisting of hydrogen, -C 1-10 alkyl, -C 2-10 alkylaryl, -C 3-6 cycloalkyl, -C 2-10 alkenyl, -C 1-10 alkylheteroaryl, -C 1-10 haloalkyl, -C 1-10 dihaloalkyl, and -C 1-10 trihaloalkyl; or a tautomer thereof; 
 
         wherein the pest infestation is caused by a population of pests comprising pesticide resistant pests. 
       
     
     
         21 . The method according to  claim 20  wherein the plant part is grain. 
     
     
         22 . The method according to  claim 20  where the pest population comprising pesticide resistance pests is selected from the group consisting of  Rhyzopertha dominica, Sitophilus oryzae, Triobolium castaneum, Oryzaephilus surinamensis  and  Cryptolestes ferrugineus.