Method for controlling particular insect pests by applying anthranilamide compounds

Abstract

This invention pertains to a method for controlling lepidopteran, homopteran, hemipteran, thysanopteran and coleopteran insect pests comprising contacting the insects or their environment with an arthropodicidally effective amount of a compound of Formula I, its N-oxide or an agriculturally suitable salt thereof wherein A and B and R 1 through R 8 are as defined in the disclosure. This invention further relates to a bezoxazinone compound of Formula 10 wherein R 4 through R 8 are as defined in the disclosure, useful for preparation of a compound of Formula I.

1 . A method for controlling lepidopteran, homopteran, hemipteran, thysanopteran and coleopteran insect pests, comprising:
 contacting the insects or their environment with an arthropodicidally effective amount of a compound of Formula I, an N-oxide or an agriculturally suitable salt thereof   
     
       
         
         
             
             
         
       
     
     wherein
 A and B are independently O or S; 
 R 1  is H, C 1 -C 6  alkyl, C 2 -C 6  alkoxycarbonyl or C 2 -C 6  alkylcarbonyl; 
 R 2  is H or C 1 -C 6  alkyl; 
 R 3  is H; C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, or C 3 -C 6  cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO 2 , hydroxy, C 1 -C 4  alkyl, C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylcarbonyl, C 3 -C 6  trialkylsilyl, phenyl, phenoxy, 5-membered heteroaromatic rings, and 6-membered heteroaromatic rings; each phenyl, phenoxy, 5-membered heteroaromatic ring, and 6-membered heteroaromatic ring optionally substituted with one to three substituents independently selected from the group consisting of C 1 -C 4  alkyl, C 2 -C 4  alkenyl, C 2 -C 4  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 4  haloalkyl, C 2 -C 4  haloalkenyl, C 2 -C 4  haloalkynyl, C 3 -C 6  halocycloalkyl, halogen, CN, NO 2 , C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 1 -C 4  alkylamino, C 2 -C 8  dialkylamino, C 3 -C 6  cycloalkylamino, C 4 -C 8  (alkyl)(cycloalkyl)amino, C 2 -C 4  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminocarbonyl, C 3 -C 8  dialkylaminocarbonyl and C 3 -C 6  trialkylsilyl; C 1 -C 4  alkoxy; C 1 -C 4  alkylamino; C 2 -C 8  dialkylamino; C 3 -C 6  cycloalkylamino; C 2 -C 6  alkoxycarbonyl or C 2 -C 6  alkylcarbonyl; 
 R 4  is H, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 6  haloalkyl, CN, halogen, C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy or NO 2 ; 
 R 5  is H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 4  alkoxyalkyl, C 1 -C 4  hydroxyalkyl, C(O)R 10 , CO 2 R 10 , C(O)NR 10 R 11 , halogen, C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, NR 10 R 11 , N(R 11 )C(O)R 10 , N(R 11 )CO 2 R 10  or S(O) n R 12 ; 
 R 6  is H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, halogen, CN, C 1 -C 4  alkoxy or C 1 -C 4  haloalkoxy; 
 R 7  is C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 6  haloalkyl, C 2 -C 6  haloalkenyl, C 2 -C 6  haloalkynyl or C 3 -C 6  halocycloalkyl; or 
 R 7  is a phenyl ring, a benzyl ring, a 5- or 6-membered heteroaromatic ring, a naphthyl ring system or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring or ring system optionally substituted with one to three substituents independently selected from R 9 ; 
 R 8  is H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, halogen, C 1 -C 4  alkoxy or C 1 -C 4  haloalkoxy; 
 each R 9  is independently C 1 -C 4  alkyl, C 2 -C 4  alkenyl, C 2 -C 4  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 4  haloalkyl, C 2 -C 4  haloalkenyl, C 2 -C 4  haloalkynyl, C 3 -C 6  halocycloalkyl, halogen, CN, NO 2 , C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 1 -C 4  alkylamino, C 2 -C 8  dialkylamino, C 3 -C 6  cycloalkylamino, C 4 -C 8  (alkyl)(cycloalkyl)amino, C 2 -C 4  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminocarbonyl, C 3 -C 8  dialkylaminocarbonyl or C 3 -C 6  trialkylsilyl; 
 R 10  is H, C 1 -C 4  alkyl or C 1 -C 4  haloalkyl; 
 R 11  is H or C 1 -C 4  alkyl; 
 R 12  is C 1 -C 4  alkyl or C 1 -C 4  haloalkyl; and 
 n is 0, 1 or 2; 
 wherein the compound of Formula I is included in a composition further comprising an effective amount of at least one additional biologically active compound or agent. 
 
   
   
       2 . The method of  claim 1  wherein
 A and B are both O;   R 7  is a phenyl ring or a 5- or 6-membered heteroaromatic ring selected from the group consisting of   
     
       
         
         
             
             
         
       
       
         each ring optionally substituted with one to three substituents independently selected from R 9 ; 
       
       Q is O, S, NH or NR 9 ; and 
       W, X, Y and Z are independently N, CH or CR 9 , provided that in J-3 and J-4 at least one of W, X, Y or Z is N. 
     
   
   
       3 . The method of  claim 2  wherein
 R 1 , R 2  and R 8  are all H;   R 3  is C 1 -C 4  alkyl optionally substituted with halogen, CN, OCH 3  or S(O) p CH 3 ;   R 4  group is attached at position 2;   R 4  is CH 3 , CF 3 , OCF 3 , OCHF 2 , CN or halogen;   R 5  is H, CH 3  or halogen;   R 6  is CH 3 , CF 3  or halogen;   R 7  is phenyl or 2-pyridinyl, each optionally substituted; and   p is 0, 1 or 2.   
   
   
       4 . The method of  claim 3  wherein
 R 3  is C 1 -C 4  alkyl and R 6  is CF 3 .   
   
   
       5 . The method of  claim 3  wherein
 R 3  is C 1 -C 4  alkyl and R 6  is Cl or Br.   
   
   
       6 . (canceled) 
   
   
       7 . The method of  claim 1  wherein the at least one additional biologically active compound or agent is selected from arthropodicides of the group consisting of pyrethroids, carbamates, neonicotinoids, neuronal sodium channel blockers, insecticidal macrocyclic lactones, γ-aminobutyric acid (GABA) antagonists, insecticidal ureas and juvenile hormone mimics. 
   
   
       8 . The method of  claim 1  wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acephate, acetamiprid, amidoflumet (S-1955), avermectin, azadirachtin, azinphos-methyl, bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb, fenoxycarb, fenpropathrin, fenproximate, fenvalerate, fipronil, flonicamid, flucythrinate, tau-fluvalinate, flufenerim (UR-50701), flufenoxuron, fonophos, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazin, novaluron, noviflumuron (XDE-007), oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, spiromesifin (BSN 2060), sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, trichlorfon and triflumuron, aldicarb, oxamyl, fenamiphos, amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben, tebufenpyrad; and biological agents such as  Bacillus thuringiensis  including ssp.  aizawai  and  kurstaki, Bacillus thuringiensis  delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi. 
   
   
       9 . The method of  claim 1  wherein the at least one additional biologically active compound or agent is selected from the group consisting of cypermethrin, cyhalothrin, cyfluthrin and beta-cyfluthrin, esfenvalerate, fenvalerate, tralomethrin, fenothicarb, methomyl, oxamyl, thiodicarb, clothianidin, imidacloprid, thiacloprid, indoxacarb, spinosad, abamectin, avermectin, emamectin, endosulfan, ethiprole, fipronil, flufenoxuron, triflumuron, diofenolan, pyriproxyfen, pymetrozine, amitraz,  Bacillus thuringiensis, Bacillus thuringiensis  delta endotoxin and entomophagous fungi. 
   
   
       10 . The method of  claim 1  wherein at least one of the insect pests controlled is selected from the group consisting of  Alabama argillacea  Hübner (cotton leaf worm),  Archips argyrospila  Walker (fruit tree leaf roller),  A. rosana  Linnaeus (European leaf roller) and other  Archips  species,  Chilo suppressalis  Walker (rice stem borer),  Cnaphalocrosis medinalis  Guenee (rice leaf roller),  Crambus caliginosellus  Clemens (corn root webworm),  Crambus teterrellus  Zincken (bluegrass webworm),  Cydia pomonella  Linnaeus (codling moth),  Earias insulana  Boisduval (spiny bollworm),  Earias vittella  Fabricius (spotted bollworm),  Helicoverpa armigera  Hübner (American bollworm),  Helicoverpa zea  Boddie (corn earworm),  Heliothis virescens  Fabricius (tobacco budworm),  Herpetogramma licarsisalis  Walker (sod webworm),  Lobesia botrana  Denis & Schiffermüller (grape berry moth),  Pectinophora gossypiella  Saunders (pink bollworm),  Phyllocnistis citrella  Stainton (citrus leafminer),  Pieris brassicae  Linnaeus (large white butterfly),  Pieris rapae  Linnaeus (small white butterfly),  Plutella xylostella  Linnaeus (diamondback moth),  Spodoptera exigua  Hübner (beet armyworm),  Spodoptera litura  Fabricius (tobacco cutworm, cluster caterpillar),  Spodoptera frugiperda  J. E. Smith (fall armyworm),  Trichoplusia ni  Hübner (cabbage looper) and  Tuta absoluta  Meyrick (tomato leafminer),  Acyrthisiphon pisum  Harris (pea aphid),  Aphis craccivora  Koch (cowpea aphid),  Aphis fabae  Scopoli (black bean aphid),  Aphis gossypii  Glover (cotton aphid, melon aphid),  Aphis pomi  De Geer (apple aphid),  Aphis spiraecola  Patch (spirea aphid),  Aulacorthum solani  Kaltenbach (foxglove aphid),  Chaetosiphon fragaefolii  Cockerell (strawberry aphid),  Diuraphis noxia  Kurdjumov/Mordvilko (Russian wheat aphid),  Dysaphis plantaginea  Paaserini (rosy apple aphid),  Eriosoma lanigerum  Hausmann (woolly apple aphid),  Hyalopterus pruni  Geoffroy (mealy plum aphid),  Lipaphis erysimi  Kaltenbach (turnip aphid),  Metopolophium dirrhodum  Walker (cereal aphid),  Macrosipum euphorbiae  Thomas (potato aphid),  Myzus persicae  Sulzer (peach-potato aphid, green peach aphid),  Nasonovia ribisnigri  Mosley (lettuce aphid),  Pemphigus  spp. (root aphids and gall aphids),  Rhopalosiphum maidis  Fitch (corn leaf aphid),  Rhopalosiphum padi  Linnaeus (bird cherry-oat aphid),  Schizaphis graminum  Rondani (greenbug),  Sitobion avenae  Fabricius (English grain aphid),  Therioaphis maculata  Buckton (spotted alfalfa aphid),  Toxoptera aurantii  Boyer de Fonscolombe (black citrus aphid), and  Toxoptera citricida  Kirkaldy (brown citrus aphid);  Adelges  spp. (adelgids);  Phylloxera devastatrix  Pergande (pecan phylloxera);  Bemisia tabaci  Gennadius (tobacco whitefly, sweetpotato whitefly),  Bemisia argentifolii  Bellows & Perring (silverleaf whitefly),  Dialeurodes citri  Ashmead (citrus whitefly) and  Trialeurodes vaporariorum  Westwood (greenhouse whitefly);  Empoasca fabae  Harris (potato leafhopper),  Laodelphax striatellus  Fallen (smaller brown planthopper),  Macrolestes quadrilineatus  Forbes (aster leafhopper),  Nephotettix cinticeps  Uhler (green leafhopper),  Nephotettix nigropictus  Stål (rice leafhopper),  Nilaparvata lugens  Stål (brown planthopper),  Peregrinus maidis  Ashmead (corn planthopper),  Sogatella furcifera  Horvath (white-backed planthopper),  Sogatodes orizicola  Muir (rice delphacid),  Typhlocyba pomaria  McAtee white apple leafhopper,  Erythroneoura  spp. (grape leafhoppers);  Magicidada septendecim  Linnaeus (periodical cicada);  Icerya purchasi  Maskell (cottony cushion scale),  Quadraspidiotus perniciosus  Comstock (San Jose scale);  Planococcus citri  Risso (citrus mealybug);  Pseudococcus  spp. (other mealybug complex);  Cacopsylla pyricola  Foerster (pear psylla),  Trioza diospyri  Ashmead (persimmon psylla),  Acrosternum hilare  Say (green stink bug),  Anasa tristis  De Geer (squash bug),  Blissus leucopterus leucopterus  Say (chinch bug),  Corythuca gossypii  Fabricius (cotton lace bug),  Cyrtopeltis modesta  Distant (tomato bug),  Dysdercus suturellus  Herrich-Schäffer (cotton stainer),  Euchistus servus  Say (brown stink bug),  Euchistus variolarius  Palisot de Beauvois (one-spotted stink bug),  Graptosthetus  spp. (complex of seed bugs),  Leptoglossus corculus  Say (leaf-footed pine seed bug),  Lygus lineolaris  Palisot de Beauvois (tarnished plant bug),  Nezara viridula  Linnaeus (southern green stink bug),  Oebalus pugnax  Fabricius (rice stink bug),  Oncopeltus fasciatus  Dallas (large milkweed bug),  Pseudatomoscelis seriatus  Reuter (cotton fleahopper),  Frankliniella occidentalis  Pergande (western flower thrip),  Scirthothrips citri  Moulton (citrus thrip),  Sericothrips variabilis  Beach (soybean thrip), and  Thrips tabaci  Lindeman (onion thrip),  Leptinotarsa decemlineata  Say (Colorado potato beetle),  Epilachna varivestis  Mulsant (Mexican bean beetle) and wireworms of the genera  Agriotes, Athous  or  Limonius ). 
   
   
       11 . A benzoxazinone compound of Formula 10 
     
       
         
         
             
             
         
       
     
     wherein
 R 4  is H, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 6  haloalkyl, CN, halogen, C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy or NO 2 ; 
 R 5  is H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 4  alkoxyalkyl, C 1 -C 4  hydroxyalkyl, C(O)R 10 , CO 2 R 10 , C(O)NR 10 R 11 , halogen, C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, NR 10 R 11 , N(R 11 )C(O)R 10 , N(R 11 )CO 2 R 10  or S(O) n R 12 ; 
 R 6  is H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, halogen, CN, C 1 -C 4  alkoxy or C 1 -C 4  haloalkoxy; 
 R 7  is C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 6  haloalkyl, C 2 -C 6  haloalkenyl, C 2 -C 6  haloalkynyl or C 3 -C 6  halocycloalkyl; or 
 R 7  is a phenyl ring, a benzyl ring, a 5- or 6-membered heteroaromatic ring, a naphthyl ring system or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring or ring system optionally substituted with one to three substituents independently selected from R 9 ; 
 R 8  is H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, halogen, C 1 -C 4  alkoxy or C 1 -C 4  haloalkoxy; 
 each R 9  is independently C 1 -C 4  alkyl, C 2 -C 4  alkenyl, C 2 -C 4  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 4  haloalkyl, C 2 -C 4  haloalkenyl, C 2 -C 4  haloalkynyl, C 3 -C 6  halocycloalkyl, halogen, CN, NO 2 , C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 1 -C 4  alkylamino, C 2 -C 8  dialkylamino, C 3 -C 6  cycloalkylamino, C 4 -C 8  (alkyl)(cycloalkyl)amino, C 2 -C 4  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminocarbonyl, C 3 -C 8  dialkylaminocarbonyl or C 3 -C 6  trialkylsilyl; 
 R 10  is H, C 1 -C 4  alkyl or C 1 -C 4  haloalkyl; 
 R 11  is H or C 1 -C 4  alkyl; 
 R 12  is C 1 -C 4  alkyl or C 1 -C 4  haloalkyl; and 
 n is 0, 1 or 2. 
 
   
   
       12 . The compound of  claim 11  wherein
 R 7  is a phenyl ring or a 5- or 6-membered heteroaromatic ring selected from the group consisting of   
     
       
         
         
             
             
         
       
       
         each ring optionally substituted with one to three substituents independently selected from R 9 ; 
       
       Q is O, S, NH or NR 9 ; and 
       W, X, Y and Z are independently N, CH or CR 9 , provided that in J-3 and J-4 at least one of W, X, Y or Z is N. 
     
   
   
       13 . The compound of  claim 12  wherein
 R 8  is H;   R 4  group is attached at position 2;   R 4  is CH 3 , CF 3 , OCF 3 , OCHF 2 , CN or halogen;   R 5  is H, CH 3  or halogen;   R 6  is CH 3 , CF 3  or halogen; and   R 7  is phenyl or 2-pyridinyl, each optionally substituted.   
   
   
       14 . The compound of  claim 13  wherein R 6  is CF 3 . 
   
   
       15 . The compound of  claim 13  wherein R 6  is Cl or Br. 
   
   
       16 . The compounds of  claim 11  wherein
 R 4  is at the 2 position and is CH 3 , Cl or Br;   R 5  is at the 4 position and is F, Cl, Br, I or CF 3 ;   R 6  is CF 3 , Cl or Br;   R 7  is 3-Cl-2-pyridinyl or 3-Br-2-pyridinyl; and   R 8  is H.   
   
   
       17 . The compound of  claim 11  wherein R 7  is 2-pyridinyl. 
   
   
       18 . The method of  claim 1  wherein a plant is contacted by a composition comprising the compound of Formula I, the N-oxide, or the agriculturally suitable salt thereof, applied as a soil drench of a liquid formulation.