Ortho-heterocyclic substituted aryl amides for controlling invertebrate pests
View Patent ↗This invention pertains to compounds of Formula I, their N-oxides and suitable salts wherein A is O or S; G is a 5- or 6-membered heteroaromatic ring or a 5- or 6-membered nonaromatic heterocyclic ring optionally including one or two ring members selected from the group consisting of C(═O), SO or S(O) 2 , each ring optionally substituted with from one to four R 2 ; each J is independently a phenyl ring, a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused carbobicyclic or heterobicyclic ring system, wherein each ring or ring system is optionally substituted with from one to four R 3 ; and R 1 , R 2 , R 3 , R 4 and n are as defined in the disclosure. A composition comprising a compound of Formula I, and a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula I are also disclosed.
1. A compound of Formula I, an N-oxide or salt thereof
wherein
A is O or S;
G is a 6-membered nonaromatic heterocyclic ring optionally including one or two ring members independently selected from the group consisting of C(═O), SO or S(O) 2 , each ring 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, C 3 -C 8 dialkylaminocarbonyl or C(═A)J;
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;
each R 6 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;
R 7 is H, C 1 -C 6 alkyl, C 1 -C 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-7 and G-43, each G optionally substituted with from one to four R 2
Q is O, S or NR 2 ;
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; and
m is an integer from 0 to 4.
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)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 H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, or
V is N; and
R 5 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.
6. The compound of claim 5 wherein
R 5 is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen or CN;
R 6 is H, CH 3 , CF 3 , OCH 2 CF 3 , OCHF 2 or halogen; and
R 7 is CH 2 CF 3 , CHF 2 or CF 3 .
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. 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.
9. The composition of claim 8 which further comprises at least one additional compound or agent for controlling an invertebrate pest.