Anthropodicidal anthranilamides
View Patent ↗This invention provides compounds of Formula 1, their N-oxides and agriculturally suitable salts wherein R 1 , R 2 , R 3 , R 4a , R 4b and R 5 are as defined in the disclosure. Also disclosed are methods for controlling invertebrate pests comprising contacting the invertebrate pests or their environment with a biologically effective amount of a compound of Formula 1 or a composition comprising a compound of Formula 1.
1. A composition comprising a biologically effective amount of a compound of Formula 1, an N-oxide or an agriculturally suitable salt thereof
wherein
R 1 is CH 3 , F, Cl or Br;
R 2 is F, Cl, Br, I or CF 3 ;
R 3 is CF 3 , Cl, Br or OCH 2 CF 3 ;
R 4a is C 1 -C 4 alkyl;
R 4b is H or CH 3 ; and
R 5 is Cl or Br;
and an effective amount of at least one additional biologically active compound or biological agent.
2. The composition of claim 1 wherein the at least one additional biologically active compound or biological 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.
3. The composition of claim 1 wherein the at least one additional biologically active compound or biological agent is selected from an insecticide, nematocide, acaricide or biological agent in the group consisting of abamectin, acephate, acetamiprid, amidoflumet, avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, 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, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamid, flucythrinate, tau-fluvalinate, flufenerim, flufenoxuron, fonophos, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazine, novaluron, noviflumuron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, spiromesifen, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, trichlorfon, triflumuron, aldicarb, fenamiphos, amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpyroximate, hexythiazox, propargite, pyridaben, tebufenpyrad, Bacillus thuringiensis ssp. aizawai and ssp. kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.
4. The composition of claim 1 wherein the at least one additional biologically active compound or biological agent is selected from an insecticide, nematocide, acaricide or biological agent in the group consisting of cypermethrin, cyhalothrin, cyfluthrin and beta-cyfluthrin, esfenvalerate, fenvalerate, tralomethrin, fenothiocarb, 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.
5. 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 1 .
6. A composition for protecting an animal from an invertebrate pest, comprising the composition of claim 1 .
7. The composition of claim 1 wherein the compound of Formula 1 is 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1 H-pyrazole-5-carboxamide.
8. The composition of claim 1 wherein the composition further comprises at least one of a surfactant, a solid diluent or a liquid diluent.
9. The composition of claim 8 wherein the composition further comprises the surfactant.
10. The composition of claim 9 wherein the surfactant is selected from the group consisting of polyethoxylated alcohols, polyethyoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers.
11. The composition of claim 10 wherein the surfactant is a polyoxypropylene/polyoxyethylene block copolymer.
12. The composition of claim 10 wherein the compound of Formula 1 is 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1 H-pyrazole-5-carboxamide.
13. The method of claim 5 wherein the compound of Formula 1 is 3 -bromo-N-[4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1 H-pyrazole-5-carboxamide.
14. The method of claim 5 wherein the composition further comprises at least one of a surfactant, a solid diluent or a liquid diluent.
15. The method of claim 14 wherein the composition further comprises the surfactant.
16. The method of claim 15 wherein the surfactant is selected from the group consisting of polyethoxylated alcohols, polyethyoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers.
17. The method of claim 16 wherein the surfactant is a polyoxypropylene/polyoxyethylene block copolymer.
18. The method of claim 16 wherein the compound of Formula 1 is 3 -bromo-N-[4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1 H-pyrazole-5-carboxamide.