Cyano anthranilamide insecticides
View Patent ↗This invention provides compounds of Formula 1, N-oxides and suitable salts thereof wherein R 1 is Me, Cl, Br or F; R 2 is F, Cl, Br, C 1 -C 4 haloalkyl or C 1 -C 4 haloalkoxy; R 3 is F, Cl or Br; R 4 is H; C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 3 -C 5 cycloalkyl, or C 4 -C 6 cycloalkylalkyl, each optionally substituted with one substituent selected from the group consisting of halogen, CN, SMe, S(O)Me, S(O) 2 Me, and OMe; R 5 is H or Me; R 6 is H, F or Cl; and R 7 is H, F or Cl. 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.
1. A method for controlling an invertebrate pest of the order of Lepidoptera or Homoptera, comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula 1, an N-oxide or a salt thereof
wherein:
R 1 is Me, Cl, Br or F;
R 2 is F, Cl, Br or C 1 -C 4 haloalkoxy;
R 3 is F, Cl or Br;
R 4 is H; C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 3 -C 5 cycloalkyl, or C 4 -C 6 cycloalkylalkyl, each optionally substituted with one substituent selected from the group consisting of halogen, CN, SMe, S(O)Me, S(O) 2 Me, and OMe;
R 5 is H or Me;
R 6 is H, F or Cl; and
R 7 is H, F or Cl.
2. A method for controlling an invertebrate pest of the order of Lepidoptera or Homoptera, comprising contacting the invertebrate pest or its environment with a biologically effective amount of a composition comprising a compound of Formula 1, an N-oxide or a salt thereof
wherein:
R 1 is Me, Cl, Br or F;
R 2 is F, Cl, Br or C 1 -C 4 haloalkoxy;
R 3 is F, Cl or Br;
R 4 is H; C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 3 -C 5 cycloalkyl, or C 4 -C 6 cycloalkylalkyl, each optionally substituted with one substituent selected from the group consisting of halogen, CN, SMe, S(O)Me, S(O) 2 Me, and OMe;
R 5 is H or Me;
R 6 is H, F or Cl; and
R 7 is H, F or Cl;
and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent;
provided that the method is other than a soil drench.
3. The method of claim 1 wherein the compound of Formula 1 is 3-bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-1-pyrazole-5-carboxamide.
4. The method of claim 2 wherein the compound of Formula 1 is 3-bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-1-pyrazole-5-carboxamide.
5. The method of claim 2 wherein the surfactant is selected from the group consisting of polyethoxylated alcohols, polyethoxylated 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.
6. The method of claim 5 wherein the surfactant is a polyoxypropylene/polyoxyethylene block copolymer.