WO2005118552B1

WO2005118552B1 - Anthranilamide insecticides

Info

Publication number: WO2005118552B1
Application number: PCT/US2005/012465
Authority: WO
Filing date: 2005-04-12
Publication date: 2006-03-02
Anticipated expiration: 2006-10-13

Abstract

This invention provides compounds of Formula (1), N oxides and suitable salts thereof, wherein R1 is Me, Cl, Br or I; R2 is Cl, Br, I or -CN; R3 is Cl, Br, CF3, OCH2CF3 or OCF2H; R4 is H; or C1-4alkyl, C2-4alkenyl or C2-4alkynyl, each optionally substituted with CN or Sme; and R5 is phenyl substituted with 1 to 3 substituents selected from the group consisting of F, Cl, Br and Me. Also disclosed are methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula (1), an N-oxide thereof or a suitable salt of the compound (e.g., as a composition described herein). This invention also pertains to a composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Formula (1), an N-oxide thereof or a suitable salt of the compound and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent.

Claims

52AMENDED CLAIMS[received by the International Bureau on 04 January 2006 (04.01.06), original claims 1 to 16 amended and replaced by new claims 1 to 15 (4 pages)]+ STATEMENTWhat is claimed is:

1. A compound of Formula 1 , an iV-oxide or a salt thereof

wherein

R¹ is Me, Cl, Br or I; R² is -CN;

R³ is Cl, Br, CF₃, OCH₂CF₃ or OCF₂H; R⁴ is H; or C1-C4 alkyl, C2-C4 alkenyl or C2-C4 alkynyl, each optionally substituted with CN or SMe; and R⁵ is phenyl substituted with 1 to 3 substituents selected from the group consisting of F, Cl, Br and Me.

2. The compound of Claim 1 wherein: R³ is Cl, Br or CF₃;

R⁴ is Me, Et, /-Pr or t-Bu; and

R⁵ is 2-chlorophenyl, 2-fluorophenyl, 2-bromophenyl, 2,4-dichlorophenyl, 2- chloro- 4-fluorophenyl, 2,6-dichlorophenyl, 2,6-difluorophenyl or 2,4,6- trichlorophenyl.

3. A composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Claim 1 and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, said composition optionally further comprising an effective amount of at least one additional biologically active compound or agent. 53

4. A composition of Claim 3 wherein at least one additional biologically active compound or agent is selected from insecticides of the group consisting of pyrethroids, carbamates, neonicotinoids, neuronal sodium channel blockers, insecticidal macrocyclic lactones, γ-aminobutyric acid antagonists, insecticidal ureas, juvenile hormone mimics, members of Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, and naturally occurring or genetically modified viral insecticides.

5. The composition of Claim 3 wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acephate, acetamiprid, acetoprole, amidoflumet, avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, bistrifluron, buprofezin, carbofuran, chlorfenapyr, chlorfiuazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamid, flucythrinate, tau-fluvalinate, fiufenerim, flufenoxuron, gamma-chalothrin, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, methoxyfenozide, metofluthrin, monocrotophos, methoxyfenozide, novaluron, noviflumuron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, protrifenbute, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, spiromesifen, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad, tralomethrin, trichlorfon, triflumuron, aldicarb, fenamiphos, amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpyroximate, hexythiazox, propargite, pyridaben, tebufenpyrad, Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, entomopathogenic virus and entomopathogenic fungi.

6. The composition of Claim 3 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, 54

fenvalerate, tralomethrin, fenothicarb, methomyl, oxamyl, thiodicarb, acetamiprid, clothianidin, imidacloprid, thiamethoxam, tbiacloprid, indoxacarb, spinosad, abamectin, avermectin, emamectin, endosulfan, ethiprole, fϊpronil, flufenoxuron, triflumuron, diofenolan, pyriproxyfen, pymetrozine, amitraz, Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis delta endotoxin and entomophagous fungi.

7. A method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Claim 1.

8. A method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a composition of Claim 3.

9. The method of Claim 7 or Claim 8 wherein the invertebrate pest is a cockroach, an ant or a termite which is contacted by the compound by consuming a bait composition comprising the compound.

10. The method of Claim 7 or Claim 8 wherein the invertebrate pest is a mosquito, a black fly, a stable, fly, a deer fly, a horse fly, a wasp, a yellow jacket, a hornet, a tick, a spider, an ant, or a gnat which is contacted by a spray composition comprising the compound dispensed from a spray container.

11. The method of Claim 8 wherein a plant is contacted with the composition applied as a soil drench of a liquid formulation.

12. The composition of Claim 3 in the form of a soil drench liquid formulation.

13. A spray composition, comprising:

(a) a compound of Claim 1; and

(b) a propellant.

14. A bait composition, comprising:

(a) a compound of Claim 1;

(b) one or more food materials; 55

(c) optionally an attractant; and

(d) optionally a humectant.

15. A device for controlling an invertebrate pest, comprising:

(a) the bait composition of Claim 14; and

(b) a housing adapted to receive the bait composition, wherein the housing has at least one opening sized to permit the invertebrate pest to pass through the opening so the invertebrate pest can gain access to the bait composition from a location outside the housing, and wherein the housing is further adapted to be placed in or near a locus of potential or known activity for the invertebrate pest.