Title of Invention	"IMINOBENZOXAZINES, IMINOBENZTHIAZINES AND IMINOQUINAZOLINES FOR CONTROLLING INVERTEBRATE PESTS"
Abstract	An iminobenzoxazine, iminobenzthiazine or iminoquinazoline compound of Formula Is or an N-oxide or a salt thereof

Full Text

WE CLAIM: 1. An iminobenzoxazine or iminobenzthiazine compound of Formula Is or an N- oxide or a salt thereof (Formula Removed) Is wherein B is O or S; J is a phenyl ring, a naphthyl ring system, a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R5; R2 is H; G; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, G, CN, NO2, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfiny 1, C1-C4 alkylsulfonyl, C2-C5 alkoxycarbonyl, C2-C6 alkylcarbonyl, C3-C6 trialkylsilyl, and a phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from R6; hydroxy; C1-C4 alkoxy; C1-C4 alkylamino; C2-C8 dialkylamino; C3-C5 cycloalkylamino; C2-C5 alkoxycarbonyl and C2-C6 alkylcarbonyl; G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C(=O), SO and S(O)2 and optionally substituted with 1 to 4 substituents selected from R3; each R3 is independently C2-C2 alkyl, halogen, CN, NO2 or C}-C2 alkoxy; each R4 is independently H, C1-C5 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CpCg .haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 haiocycloalkyl, halogen, CN, NO2, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C1- C4 alkylthio, C1-C4 alkylsulfmyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C5 alkoxyalkyl, C1-C4 hydroxyalkyl, C(O)R10, CO2R10, C(O)NR10R11, NR10R11, N(R11)CO2R10 or C3-C6 trialkylsilyl; or each R4 is independently a phenyl, benzyl, phenoxy or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from R6; each R5 is independently C1-C6 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, CO2H, CONH2, NO2, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfmyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkylcarbonyi, C2-C6 alkoxycarbonyl, C2-C5 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C5 trialkylsilyl; or each R5 is independently a phenyl, benzyl, benzoyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from R6; or two R5 groups when attached to adjacent carbon atoms are taken together as —OCF2O— , —CF2CF2O—, or—OCF2CF2O—; each R6 is independently C1-C6 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfr)nyl, C1-C4 alkylamino, C2-Cg dialkylamino, C3-C5 cycloalkylamino, C4-C8 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C3-C5 trialkylsiiyl, or C1-C4 haloalkylthio; R10 is H, C1-C4 alkyl or C1-C4 haloalkyl; R11 is H or C1-C4 alkyl; and n is an integer from 1 to 4, with the proviso that (a) when B is S, each R4 is H, and R2 is methyl or ethyl, then J is not 2,4,6-I trimethylphenyl; (b) when B is S, each R4 is H, and R2 is ethyl or isopropyl, then J is not unsubstituted phenyl or 2-chlorophenyl; (c) when B is S, each R4 is H, and R4 is isopropyl then J is not 2-methylphenyl; (d) when B is O, each R4 is H, and R2 is methyl, then J is not unsubstituted phenyl or unsubstituted 2-pyrolyl; and (e) when B is S, each R4 is H, and R2 is H then J is not unsubstituted phenyl. 2. The compound as claimed in claim 1 wherein J is a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3, J-4 and J-5, each J optionally substituted with 1 to 3 R5 (Formula Removed) Q is O, S,NH or NR5;and W, X, Y and Z are independently N, CH or CR5, provided that in J-4 and J-5 at least one of W,X,YorZisN;and each R5 is independently C1-C6 alkyl, C1-C6 haloalkyl, C3-C5 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl or C2-C4 alkoxycarbonyl; or a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from R6. 3 The compound as claimed in claim 2 wherein J substituted with 1 to 3 R5 is selected from the group consisting of J-6, J-7, J-8, J-9, J-10, J-11,J-12 and J-13 (Formula Removed) V is N, CH, CF, CCl, CBr or CI; each R6a is independently H or R6; R6 is C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, halogen, CN, C1-C4 alkoxy, C1-C4 haloalkoxy or C1-C4 haloalkylthio; each R7 is independently C2-C5 alkyl, C1-C5 haloalkyl, halogen, CN, C1-C4 alkoxy, C1-C4 haloalkoxy or C1-C4 haloalkylthio; R9 is C2-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl or C3-C5 haloalkynyl; R10 is C1-C4 alkyl or C1-C4 haloalkyl; R11 is C1-C4 alkyl; and n is 1 or 2. 4. The compound as claimed in claim 3 wherein R2 is C1-C4 alkyl optionally substituted with halogen, CN, OCH3 or S(O)pCH3; or CH2C=CH; one R4 group is attached to the phenyl ring at the 2-position and said R^ is CH3, CF3, OCF3, OCHF2, S(O)pCF3, S(O)pCHF2, CN or halogen; a second R4 is H, F, Cl, Br, I or CF3; R6a is H, C1-C4 alkyl, C1-C4 haloalkyl, halogen or CN; R7 is CH3, CF3, OCH2CF3, OCHF2 or halogen; R9 is C2-C6 alkyl or C1-C6 haloalkyl; and p is 0, 1 or 2. 5. The compound as claimed in claim 4 wherein J substituted with 1 to 3 R5 is J-6; V is N or CH; and R7 is CH3, CF3, OCH2CF3, OCHF2 or halogen. 6. The compound as claimed in claim 5 wherein R6a is F, C1 or Br; and R7 is halogen or CF3. 7. The compound as claimed in claim 4 wherein J substituted with 1 to 3 R5 is J-7. 8. The compound as claimed in claim 4 wherein J substituted with 1 to 3 R5 is J-8; V is N; R6 is C1 or Br; and R7 is halogen or CF3. 9. The compound as claimed in claim 4 wherein J substituted with 1 to 3 R5 is J-9; R6a is C1 or Br; and R7 is CF3. 10. The compound as claimed in claim 4 wherein J substituted with 1 to 3 R5 is J-10; R6a is C1 or Br; and R9 is CH2CF3, CHF2 or CF3. 11. The compound as claimed in claim 4 wherein J substituted with 1 to 3 R5 is J-11; R6a is C1 or Br; and R7 is halogen, OCH2CF3, OCHF2 or CF3. 12. The compound as claimed in claim 4 wherein J substituted with 1 to 3 R5 is J-12; R6a is C1 or Br; R7 is halogen, OCH2CF3, OCHF2 or CF3; and R9 is CH2CF3, CHF2 or CF3. 13. The compound as claimed in claim 4 wherein J substituted with 1 to 3 R5 is J-13; R6a is C1 or Br; and R9 is CH2CF3, CHF2 or CF3. 14. The compound as claimed in claim 5 selected from the group consisting of: N-[2-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-4H-3,1- benzoxazin-4-ylidene]methanamine, N-[2-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-4H-3,1- benzoxazin-4-ylidene]-2-propanamine, N-[2-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-4H-3,1- benzoxazin-4-ylidene]ethanamine, N-[6-chloro-2-[3-chloro-l-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1- benzoxazin-4-ylidene]methanamine, N-[6-chloro-2-[3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1 - benzoxazin-4-yIidene]-2-propanamine, N-[6-chloro-2-[3-chloro-1-(3-chloro-2-pyridinyI)-1H-pyrazol-5-yl]-8-methyl-4H-3,l- benzoxa2m-4-yIidene]ethanamine, N-[6-chloro-2-[l-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl- 4H-3,1 -benzoxazin-4-ylidene]methanamine, N-[6-chloro-2-[l-(3-chloro-2-pyridinyl)-3-(trifluorornethyl)-1H-pyrazol-5-yl]-8-methyl- 4H-3,l-benzoxazm-4-ylidene]-2-propanamme, N-[6-chloro-2-[1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl- 4H-3,1 -benzoxazin-4-ylidene]ethanamine, N-[6-chloro-2-[l-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl- 4H-3,l-benzoxazin-4-ylidene]-2-methyl-2-propanamine, N-[2-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazoI-5-yl]-8-methyi-4H-3,1 - benzoxazin-4-ylidene]-2-propanamine, N-[2-[3-bromo-1-(3-chioro-2-pyridinyl)-1H-pyrazol-5-yl]-8-methy}-4H-3,1- benzoxazin-4-ylidene]-2-methyl-2-propanamine, N-[2-[l-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,l- benzoxazin-4-ylidene]-2-propanamine and N-[2-[l-(3-chloro-2-pyridinyi)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,l- benzoxazm-4-ylidene]-2-methyl-2-propanamine. 15. A composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Formula Is as claimed in claim 1 in a weight percent from 0.01% to 99.0% and at least one additional component in a weight percent selected from the group consisting of surfactants in a weight percent from 0% to 15% selected from polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, diaikyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers, solid diluents in a weight percent from 5% to 99.9% selected from bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate, and liquid diluents in a weight percent from 5% to 99.9% selected from water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, com, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol, said composition optionally further comprising an effective amount of at least one additional biologically active compound or agent in a weight percent from 0.01% to 99.0% selected from abamectin, acephate, acetamiprid, 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, flufenoxuron, fonophos, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazin, novaluron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, trichlorfon and triflumuron; fungicides selected from 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, (5)-3,5-dichloro-N-(3-chloro-1-ethyi-l-methyl-2-oxopropyl)-4-methylbenzamide (RH 7281), diclocymet (S-2900), diclomezine, dicloran, difenoconazole, (5}-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), fluquinconazole, flusiiazole, flutolanil, flutriafol, folpet, fosetyl-aluminum, furalaxyl, fiirametapyr (S-82658), hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl, metconazole, metomino-strobin/fenominostrobin (SSF-126), myclobutani!, neo-asozin (ferric methane-arsonate), oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb, propiconazole, pyrifenox, pyraclostxobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin and vinclozolin; nematocides selected from aldicarb, oxamyl and fenamiphos; bactericides selected from streptomycin; acaricides selected from amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; and biological agents selected from Bacillus thuringiensis including ssp. aizawai and kurstaki. Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.

Documents:

587-DELNP-2004-Abstract-(30-12-2010).pdf

587-delnp-2004-abstract.pdf

587-DELNP-2004-Claims-(30-12-2010).pdf

587-DELNP-2004-claims-03-11-2011.pdf

587-delnp-2004-claims.pdf

587-DELNP-2004-Correspondence Others-(04-11-2011)..pdf

587-DELNP-2004-Correspondence-Others-(30-12-2010)-.pdf

587-delnp-2004-correspondence-others.pdf

587-delnp-2004-description (complete).pdf

587-delnp-2004-form-1.pdf

587-DELNP-2004-Form-2-(30-12-2010).pdf

587-delnp-2004-form-2.pdf

587-DELNP-2004-Form-3-(30-12-2010).pdf

587-delnp-2004-form-3.pdf

587-delnp-2004-form-5.pdf

587-DELNP-2004-GPA-(30-12-2010)-.pdf

587-delnp-2004-pct-101.pdf

587-delnp-2004-pct-408.pdf

587-DELNP-2004-Petition 137-(30-12-2010)-.pdf

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