Anthranilamide arthropodicide treatment

Abstract

This invention pertains to methods for protecting a propagule or a plant grown therefrom from invertebrate pests comprising contacting the propagule or the locus of the propagule with a biologically 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 also relates to propagules treated with a compound of Formula I and compositions comprising a Formula I compound for coating propagules.

1 . A method for protecting from a propagule or a plant grown therefrom from an invertebrate pest, comprising:
 contacting the propagule or the locus of the propagule with a biologically effective amount of a compound of Formula I, an N-oxide thereof 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. 
 
   
   
       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 ; 
       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 . A propagule contacted with a biologically effective amount of a compound of Formula I according to  claim 1 , an N-oxide thereof or an agriculturally suitable salt thereof; provided that the propagule is not a seed. 
   
   
       7 . (canceled) 
   
   
       8 . (canceled) 
   
   
       9 . (canceled) 
   
   
       10 . The propagule of  claim 6  which is a rhizome, tuber, bulb or corm, or viable division thereof. 
   
   
       11 . The propagule of  claim 10  which is a rhizome, tuber, bulb or corm, or viable division thereof, of potato, sweet potato, yam, garden onion, tulip, gladiolus, lily, narcissus, dahlia, iris, crocus, anemone, hyacinth, grape-hyacinth, freesia, ornamental onion, wood-sorrel, squill, cyclamen, glory-of-the-snow, striped squill, calla lily, gloxinia or tuberous begonia. 
   
   
       12 . The propagule of  claim 11  which is a rhizome, tuber, bulb or corm, or viable division thereof, of potato, sweet potato, garden onion, tulip, daffodil, crocus or hyacinth. 
   
   
       13 . The propagule of  claim 6  which is a stem or leaf cutting. 
   
   
       14 . The propagule of  claim 6  coated with a composition comprising (1) a biologically effective amount of a compound of Formula I, an N-oxide thereof or an agriculturally suitable salt thereof, and (2) a film former or adhesive agent. 
   
   
       15 . (canceled) 
   
   
       16 . An invertebrate pest control composition for coating a propagule, the composition comprising (1) a biologically effective amount of a compound of Formula I according to  claim 1 , an N-oxide thereof or an agriculturally suitable salt thereof, and (2) a film former or adhesive agent. 
   
   
       17 . The composition according to  claim 16  wherein the film former or adhesive agent is selected from the group consisting of polyvinyl acetates, polyvinyl acetate copolymers, hydrolyzed polyvinyl acetates, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers, polyvinyl methyl ether, polyvinyl methyl ether-maleic anhydride copolymer, waxes, latex polymers, celluloses including ethylcelluloses and methylcelluloses, hydroxymethylcelluloses, hydroxypropylcellulose, hydroxymethylpropylcelluloses, polyvinylpyrrolidones, alginates, dextrins, malto-dextrins, polysaccharides, fats, oils, proteins, karaya gum, jaguar gum, tragacanth gum, polysaccharide gums, mucilage, gum arabics, shellacs, vinylidene chloride polymers and copolymers, lignosulfonates, acrylic copolymers, starches, polyvinylacrylates, zeins, gelatin, carboxymethylcellulose, chitosan, polyethylene oxide, acrylimide polymers and copolymers, polyhydroxyethyl acrylate, methylacrylimide monomers, alginate, ethylcellulose, polychloroprene and syrups or mixtures thereof. 
   
   
       18 . The composition according to  claim 17  wherein the film former or adhesive agent is selected from polymers and copolymers of vinyl acetate, poly-vinylpyrrolidone-vinyl acetate copolymer and water-soluble waxes. 
   
   
       19 . The composition according to  claim 16  further comprising an effective amount of at least one additional biologically active compound or agent. 
   
   
       20 . The composition according to  claim 19  wherein 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. 
   
   
       21 . The composition according to  claim 19  wherein 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. 
   
   
       22 . The composition according to  claim 19  wherein at least one additional biologically active compound or agent is selected from fungicides of the group consisting of acibenzolar, azoxystrobin, benomyl, blasticidin-S, Bordeaux mixture (tribasic copper sulfate), bromuconazole, carpropamid, captafol, captan, carbendazim, chloroneb, chlorothalonil, copper oxychloride, copper salts, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, (S)-3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (RH 7281), diclocymet (S-2900), diclomezine, dicloran, difenoconazole, (S)-3,5-dihydro-5-methyl-2-(methylthio)-5-phenyl-3-(phenylamino)-4H-imidazol-4-one (RP 407213), dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dodine, edifenphos, epoxiconazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fencaramid (SZX0722), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, fluazinam, fludioxonil, flumetover (RPA 403397), flumorf/flumorlin (SYP-L190), fluoxastrobin (HEC 5725), fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminum, furalaxyl, furametapyr (S-82658), hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl, metconazole, metominostrobin/fenominostrobin (SSF-126), metrafenone (AC 375839), myclobutanil, neo-asozin (ferric methanearsonate), nicobifen (BAS 510), orysastrobin, oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb, propiconazole, proquinazid (DPX-KQ926), prothioconazole (JAU 6476), pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin and vinclozolin. 
   
   
       23 . The composition according to  claim 19  wherein at least one additional biologically active compound or agent is selected from fungicides in the group consisting of thiram, maneb, mancozeb and captan.