IP Library › Granted Patent US 8,623,890

Granted Patent B2

US 8,623,890 · App. 13/264,159 · Granted Jan 7, 2014

Nematocidal sulfonamides

Inventors: George Philip Lahm (Wilmington, DE); Renee M. Lett (Newark, DE); Brenton Todd Smith (Exton, PA); Benjamin Kenneth Smith (Newark, DE); C. Anne Daly (Middletown, DE)

Assignee: E I du Pont de Nemours and Company

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Quick Facts

Patent No.: US 8,623,890
App. No.: 13/264,159
Granted: Jan 7, 2014
Kind: B2

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Abstract

Disclosed are compounds of Formula 1, N-oxides, and salts thereof, wherein Z is O or S; and R 1 , R 2 , R 3 , Q and n are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling a parasitic nematode comprising contacting the parasitic nematode or its environment with a biologically effective amount of a compound or a composition of the invention.

Claims (154)

1. A compound selected from Formula 1, an N-oxide, or a salt thereof,

wherein

Z is O or S;

each R 1 is independently halogen, cyano, nitro, SF 5 , OCN, SCN, Si(R 15 ) 3 , OR 4 , NR 5 R 6 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7 , OC(O)OR 8 , OC(O)NR 11 R 12 , OS(O) 2 R 9 , OS(O) 2 NR 11 R 12 , N(R 10 )C(O)R 7 , N(R 10 )C(O)NR 11 R 12 , N(R 10 )S(O) 2 R 9 or N(R 10 )S(O) 2 NR 11 R 12 ; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or C 1 -C 6 alkyl substituted with 1 to 4 substituents independently selected from the group consisting of cyano, nitro, OR 4 , NR 5 R 6 , C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 and S(O) 2 NR 11 R 12 ; or phenyl, naphthalenyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 6 alkoxyalkyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a ;

R 2 is H, halogen, cyano, nitro, SF 5 , OCN, SCN, Si(R 15 ) 3 , OR 4 , NR 5 R 6 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7 , OC(O)OR 8 , OC(O)NR 11 R 12 , OS(O) 2 R 9 , OS(O) 2 NR 11 R 12 , N(R 10 )C(O)R 7 , N(R 10 )C(O)NR 11 R 12 , N(R 10 )S(O) 2 R 9 or N(R 10 )S(O) 2 NR 11 R 12 ; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or C 1 -C 6 alkyl substituted with 1 to 4 substituents independently selected from the group consisting of cyano, nitro, OR 4 , NR 5 R 6 , C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 and S(O) 2 NR 11 R 12 ; or phenyl, naphthalenyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 6 alkoxyalkyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a ;

R 3 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 or S(O) 2 NR 11 R 12 ; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or C 1 -C 6 alkyl substituted with 1 to 4 substituents independently selected from the group consisting of cyano, nitro, OR 4 , NR 5 R 6 , C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 and S(O) 2 NR 11 R 12 ; or C 1 -C 6 alkyl substituted with 1 or 2 substituents independently selected from the group consisting of phenyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 6 alkoxyalkyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a ; or phenyl optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 6 alkoxyalkyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a ;

Q is phenyl, naphthalenyl, a 5- or 6-membered heteroaromatic ring or an 8- to 10-membered heteroaromatic bicyclic ring system, each optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, SF 5 , OCN, SCN, Si(R 15 ) 3 , OR 4 , NR 5 R 6 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C(X)R 7 , C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7 , OC(O)OR 8 , OC(O)NR 11 R 12 , OS(O) 2 R 9 , OS(O) 2 NR 11 R 12 , N(R 10 )C(O)R 7 , N(R 10 )C(O)NR 11 R 12 , N(R 10 )S(O) 2 R 9 , N(R 10 )S(O) 2 NR 11 R 12 and R 14 ;

each X is independently O or S;

each R 4 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, each substituted with 1 to 4 substituents independently selected from the group consisting of cyano, nitro, OR 4a , NR 5a R 6a , C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , S(O) m R 9a or S(O) 2 NR 11 R 12 ; or phenyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 2 -C 6 alkoxyalkyl, S(O) m R 9a , S(O) 2 NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a ;

each R 4a is independently H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 5 is independently H, NR 5a R 6a , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 or S(O) 2 NR 11 R 12 ; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or phenyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 2 -C 6 alkoxyalkyl, S(O) m R 9a , S(O) 2 NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a ;

each R 5a is independently H or C 1 -C 6 alkyl;

each R 6 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ;

each R 6a is independently H, C 1 -C 6 alkyl, C(O)R 13 or C(O)OR 13 ;

each R 7 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or phenyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 2 -C 6 alkoxyalkyl, S(O) m R 9a , S(O) 2 NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a ;

each R 7a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 8 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, each substituted with 1 to 4 substituents independently selected from the group consisting of cyano, nitro, OR 4 , NR 5 R 6 , C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 and S(O) 2 NR 11 R 12 ; or phenyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 2 -C 6 alkoxyalkyl, S(O) m R 9a , S(O) 2 NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a ;

each R 8a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 9 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, each substituted with 1 to 4 substituents independently selected from the group consisting of cyano, nitro, OR 4 , NR 5 R 6 , C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 and S(O) 2 NR 11 R 12 ; or phenyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 2 -C 6 alkoxyalkyl,

each R 9a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 10 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , S(O) m R 9a or S(O) 2 NR 11 R 12 ;

each R 10a is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl;

each R 11 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, each substituted with 1 to 4 substituents independently selected from the group consisting of cyano, nitro, OR 4a , NR 5a R 6a , C(X)R 7a , C(O)OR 8a , C(O)NR 11a R 12 , S(O) m R 9a or S(O) 2 NR 11a R 12 ; or phenyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11a R 12 , OR 4a , C 2 -C 6 alkoxyalkyl, S(O) m R 9a , S(O) 2 NR 11a R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10a )C(O)R 7a ;

each R 11a is independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl;

each R 12 is independently H, NR 5a R 6a , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 or S(O) 2 NR 11 R 12 ; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or phenyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 , OR 4a , C 2 -C 6 alkoxyalkyl, S(O) m R 9a , S(O) 2 NR 11 R 12 , NR 5a R 6a , OC(O)R 7a and N(R 10 )C(O)R 7a ;

each R 13 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ;

each R 14 is independently C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, each substituted with 1 to 4 substituents independently selected from the group consisting of cyano, nitro, OR 4 , NR 5 R 6 , C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 and S(O) 2 NR 11 R 12 ; or phenyl, naphthalenyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 6 alkoxyalkyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a ;

each R 15 is independently C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl; or C 3 -C 7 cycloalkyl, C 4 -C 8 cycloalkylalkyl or C 5 -C 7 cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, OR 4a and S(O) m R 9a ; or phenyl optionally substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 6 alkoxyalkyl, C(X)R 7 , C(O)OR 8 , C(O)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a ;

each m is independently 0, 1 or 2; and

n is 0, 1, 2, 3 or 4;

provided that when n is 2 and one R 1 is CF 3 in the 3-position of Formula 1 and the other R 1 is Cl in the 5-position of Formula 1, and R 2 and R 3 are H, then Q is other than 2-chlorophenyl, 2-chloro-6-methylphenyl, 2,6-dichlorophenyl, 2-chloro-4-fluorophenyl, 2,5-bis(2,2,2-trifluoroethoxy)phenyl, 2,4,6-trichlorophenyl, 2-chloro-5-(trifluoromethyl)phenyl or 3,5-dimethyl-4-isoxazolyl.

2. A compound of claim 1 wherein:

Z is O; and

Q is phenyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 6 alkoxyalkyl, C(X)R 7 , C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a .

3. A compound of claim 2 wherein:

Q is phenyl, pyridyl, pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, furanyl or thienyl, each optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, OR 4 , NR 5 R 6 , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 6 alkoxyalkyl, C(X)R 7 , C(O)OR 8 , C(X)NR 11 R 12 , S(O) m R 9 , S(O) 2 NR 11 R 12 , OC(O)R 7a and N(R 10 )C(O)R 7a .

4. A compound of claim 2 or 3 wherein:

each R 1 is independently halogen, cyano, nitro, OR 4 , C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

R 2 is H, halogen or C 1 -C 6 alkyl;

R 3 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(X)R 7 , C(O)OR 8 or S(O) m R 9 ; or C 1 -C 6 alkyl substituted with 1 or 2 OR 4 ; and

n is 1 or 2.

5. A compound of claim 1 that is selected from the group consisting of:

8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide,

8-chloro-N-[(4-cyano-2,5-dimethylphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide,

N-[(5-acetyl-2-chlorophenyl)sulfonyl]-8-chloro-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide,

8-chloro-N-[(3-methyl-2-thienyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide,

8-chloro-N-[(4-methyl-2-thienyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide,

8-chloro-N-[(3-chloro-1-methyl-1H-pyrazol-4-yl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide,

8-chloro-N-[(5-methoxy-2-nitrophenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide;

8-chloro-N-[(2-chloro-5-ethylphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide,

8-chloro-N-[(1-ethyl-3-methyl-1H-pyrazol-4-yl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide,

8-bromo-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide,

N-[(2-bromo-5-methylphenyl)sulfonyl]-8-chloro-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide,

8-chloro-N-[(2-chloro-5-methylphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide,

8-chloro-N-[(3-chloro-1-ethyl-1H-pyrazol-4-yl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide, and

N-[(5-acetyl-2-methylphenyl)sulfonyl]-8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide.

6. A composition comprising a compound of Formula 1, an N-oxide, or a salt thereof,

wherein

Z is O or S;

each X is independently O or S;

each R 4a is independently H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 5a is independently H or C 1 -C 6 alkyl;

each R 6a is independently H, C 1 -C 6 alkyl, C(O)R 13 or C(O)OR 13 ;

each R 7a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 8a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 9a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 10a is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl;

each R 11a is independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl;

each m is independently 0, 1 or 2; and

n is 0, 1, 2, 3 or 4;

and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.

7. The composition of claim 6 wherein said composition further comprises at least one additional biologically active compound or agent.

8. The composition of claim 7 wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, bistrifluoron, borate, buprofezin, carbaryl, carbofuran, cartap, carzol, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezin, clothianidin, cyantraniliprole, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenbutatin oxide, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, flufenerim, flufenoxuron, fluvalinate, tau-fluvalinate, fonophos, formetanate, fosthiazate, halofenozide, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, indoxacarb, insecticidal soaps, isofenphos, lufenuron, malathion, metaflumizone, metaldehyde, methamidophos, methidathion, methiodicarb, methomyl, methoprene, methoxychlor, metofluthrin, monocrotophos, methoxyfenozide, nitenpyram, nithiazine, novaluron, noviflumuron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargite, protrifenbute, pymetrozine, pyrafluprole, pyrethrin, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulprofos, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, tetramethrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad, tralomethrin, triazamate, trichlorfon, triflumuron, all strains of Bacillus thuringiensis , entomopathogenic bacteria, all strains of Nucleo polyhydrosis viruses, entomopathogenic viruses and entomopathogenic fungi.

9. The composition of claim 8 wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acetamiprid, acrinathrin, amitraz, avermectin, azadirachtin, bifenthrin, buprofezin, carbaryl, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flonicamid, flubendiamide, flufenoxuron, fluvalinate, formetanate, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, lufenuron, metaflumizone, methiodicarb, methomyl, methoprene, methoxyfenozide, nitenpyram, nithiazine, novaluron, oxamyl, pymetrozine, pyrethrin, pyridaben, pyridalyl, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, tebufenozide, tetramethrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumuron, all strains of Bacillus thuringiensis and all strains of Nucleo polyhydrosis viruses.

10. A method for controlling a parasitic nematode comprising contacting the parasitic nematode or its environment with a biologically effective amount of a compound of Formula 1, an N-oxide, or a salt thereof,

wherein

Z is O or S;

each X is independently O or S;

each R 4a is independently H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 5a is independently H or C 1 -C 6 alkyl;

each R 6a is independently H, C 1 -C 6 alkyl, C(O)R 13 or C(O)OR 13 ;

each R 7a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 8a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 9a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 10a is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl;

each R 11a is independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl;

each m is independently 0, 1 or 2; and

n is 0, 1, 2, 3 or 4.

11. The method of claim 10 wherein the environment is a plant.

12. The method of claim 10 wherein the environment is a seed.

13. The method of claim 12 wherein the seed is coated with the compound of Formula 1, an N-oxide or salt thereof, formulated as a composition comprising a film former or adhesive agent.

14. A treated seed comprising a compound of Formula 1, an N-oxide, or a salt

wherein

Z is O or S;

each X is independently O or S;

each R 4a is independently H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 5a is independently H or C 1 -C 6 alkyl;

each R 6a is independently H, C 1 -C 6 alkyl, C(O)R 13 or C(O)OR 13 ;

each R 7a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 8a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 9a is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

each R 10 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C(X)R 7a , C(O)OR 8a , C(O)NR 11 R 12 ; S(O) m R 9a or S(O) 2 NR 11 R 12 ;

each R 10a is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl or C 2 -C 6 haloalkynyl;

each R 11a is independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl;

each m is independently 0, 1 or 2; and

n is 0, 1, 2, 3 or 4;

in an amount of from about 0.0001 to 1% by weight of the seed before treatment.

Assignments (1)

NUNC PRO TUNC ASSIGNMENT Recorded Nov 29, 2022

From: E.I. DU PONT DE NEMOURS AND COMPANY

To: CORTEVA AGRISCIENCE LLC

Reel/Frame 063141/0155 →

Continuity (2)

Provisional Application 61175206 · May 4, 2009

Related Publication 20120114624A1 · May 10, 2012