Ortho-heterocyclic substituted aryl amides for controlling invertebrate pests

1. A compound of Formula I, an N-oxide or salt thereof

wherein

A is O or S;

G is a 5- membered heteroaromatic ring with at least one ring member being nitrogen, optionally substituted with from one to four R 2 ;

J is a pyrazole ring selected from the group consisting of J-5, J-6 and J-7, each ring substituted with R 3 and optionally substituted with R 6 or R 7 ;

R 1 is H; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl each optionally substituted with one or more substituents independently selected from the group consisting of halogen, CN, NO 2 , hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkoxycarbonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino and C 3 -C 6 cycloalkylamino; or

R 1 is C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl or C 3 -C 8 dialkylaminocarbonyl;

each R 2 is independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, CO 2 H, CONH 2 , NO 2 , hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 6 cycloalkylamino, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 8 dialkylaminocarbonyl or C 3 -C 6 trialkylsilyl; or

each R 2 is independently a phenyl, benzyl, benzoyl, phenoxy or 5- or 6-membered heteroaromatic ring, a naphthyl ring system, or an aromatic or nonaromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring or ring system substituted with from one to three substituents independently selected from R 5 ;

R 3 is pyridine substituted with from one to three substituents independently selected from R 5 ;

each R 4 is independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, NO 2 , hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 6 cycloalkylamino, or C 3 -C 6 trialkylsilyl; or

each R 4 is independently a phenyl, benzyl or phenoxy ring, each ring substituted with from one to three substituents independently selected from R 5 ;

each R 5 is independently H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 6 cycloalkylamino, C 4 -C 7 (alkyl)cycloalkylamino, C 2 -C 4 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 8 dialkylaminocarbonyl or C 3 -C 6 trialkylsilyl;

R 6 is H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, halogen, CN, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 haloalkylthio;

variable R 7 is H, C 1 -C 6 alkyl, C 1-6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl or C 3 -C 6 haloalkynyl; and

n is an integer from 1 to 4.

2. The compound of claim 1 wherein

A is O;

G is selected from the group consisting of G-1, G-2 and G-3, each G optionally substituted with from one to four R 2

Q is O, S or NR 2 ;

X, Y and Z are independently N or CR 2 provided that in G-1 and G-2 at least one of Q, X, Y and Z is N; and

one R 4 group is attached to remainder of Formula I at either the 2-position or 5-position of the phenyl ring, and said R 4 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen, CN, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl.

3. The compound of claim 2 wherein

R 1 is H or C 2 -C 6 alkyl; and

n is 1 or 2.

4. The compound of claim 3 wherein

R 1 is H;

one R 4 is attached to remainder of Formula I at the 2-position of the phenyl ring ortho to the NR 1 C(=A)J moiety and is selected from the group consisting of C 1 -C 3 alkyl, CF 3 , OCF 3 , OCHF 2 , S(O) p CF 3 , S(O) p CHF 2 and halogen and optionally a second R 4 is attached at the 4-position of the phenyl ring para to the NR 1 C(=A)J moiety and is selected from the group consisting of halogen, C 1 -C 3 alkyl and C 1 -C 3 haloalkyl; and

p is 0, 1 or 2.

5. The compound of claim 4 wherein

R 3 is

V is N; and

each R 5 is independently H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, halogen, CN, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 haloalkylthio.

6. The compound of claim 5 wherein

R 5 is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen or CN; and

R 6 is H, CH 3 , CF 3 , OCH 2 CF 3 , OCHF 2 or halogen.

7. The compound of claim 6 wherein J substituted with R 3 and optionally substituted with R 6 is J-5; R 5 is Cl or Br; and R 6 is halogen, OCH 2 CF 3 , OCHF 2 or CF 3 .

8. The compound of claim 1 which is

1-(3-chloro-2-pyridinyl)-N-[2-(1H-imidazol-2-yl)-6-methylphenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide.

9. 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 surfactants, solid diluents and liquid diluents.

10. The composition of claim 9 which further comprises at least one additional compound or agent for controlling an invertebrate pest.