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 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. The compound of claim 1 wherein
R 1 is Me or Cl;
R 2 is Cl, Br, OCF 2 H, OCF 3 or OCH 2 CF 3 ; and
R 4 is H, Me, Et, i-Pr, t-Bu, CH 2 CN, CH(Me)CH 2 SMe or C(Me) 2 CH 2 SMe.
3. The compound of claim 2 wherein:
R 2 is Cl, Br, or OCH 2 CF 3 ;
R 4 is H, Me, Et or i-Pr; and
R 5 is H.
4. 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.
5. The composition of claim 4 in the form of a soil drench liquid formulation.
6. A method for controlling an invertebrate pest comprising contacting a plant with a biologically effective amount of a composition of claim 5 as a soil drench.
7. A compound of Formula 1 selected from the group consisting of
3-chloro-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide,
3-chloro-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-(aminocarbonyl)phenyl]-1H-pyrazole-5-carboxamide,
3-bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide,
3-bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-(aminocarbonyl)phenyl]-1H-pyrazole-5-carboxamide,
3-chloro-1-(3-chloro-2-pyridinyl)-N-[2-chloro-4-cyano-6-[(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide,
3-bromo-N-[2-chloro-4-cyano-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide,
3-chloro-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide,
3-bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide,
1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-[(dimethylamino)carbonyl]-6-methylphenyl]-3-(2,2,2-trifluoroethoxy)-1H-pyrazole-5-carboxamide,
1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-3-(2,2,2-trifluoroethoxy)-1H-pyrazole-5-carboxamide,
3-chloro-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-[(cyclopropylamino)carbonyl]-6-methylphenyl]-1H-pyrazole-5-carboxamide, and
3-bromo-1-(3-chloro-2-pyridinyl)-N-[4-cyano-2-[[(cyclopropylmethyl)amino]carbonyl]-6-methylphenyl]-1H-pyrazole-5-carboxamide.