US 7,541,377 B2
Substituted anthranilamides for controlling invertebrate pests
Bruce Lawrence Finkelstein, Newark, Del. (US); George Philip Lahm, Wilmington, Del. (US); Stephen Frederick McCann, Newark, Del. (US); Thomas Paul Selby, Hockessin, Del. (US); Ying Song, Hockessin, Del. (US); and Thomas Martin Stevenson, Newark, Del. (US)
Assigned to E.I. du Pont de Nemours and Company, Wilmington, Del. (US)
Filed on Jan. 31, 2007, as Appl. No. 11/700,584.
Application 11/700584 is a division of application No. 10/486312, granted, now 7,199,138, previously published as PCT/US02/26960, filed on Aug. 13, 2002.
Claims priority of provisional application 60/312680, filed on Aug. 16, 2001.
Prior Publication US 2007/0203201 A1, Aug. 30, 2007
Int. Cl. A01N 43/56 (2006.01); C07D 231/12 (2006.01); C07D 231/34 (2006.01)
U.S. Cl. 514—406  [514/407; 548/369.7; 548/375.1] 17 Claims
 
1. A compound of Formula I, an N-oxide or a salt thereof,

OG Complex Work Unit Drawing
wherein
A and B are independently O or S;
X is CR10;
Y is N;
R1 is H; R11; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of R6, halogen, CN, NO2, hydroxy, C1-C4 alkoxy, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, and R11;
R2 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl or C2-C6 alkylcarbonyl;
R3 is H; R11; C1-C4 alkoxy; C1-C4 alkylamino; C2-C8 dialkylamino; C3-C6 cycloalkylamino; C2-C6 alkoxycarbonyl; C2-C6 alkylcarbonyl; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of R6, halogen, CN, NO2, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 trialkylsilyl, R11, a phenyl ring, and a phenoxy ring, each phenyl or phenoxy ring optionally substituted with from one to three substituents independently selected from W and optionally substituted with one R12;
R4 is C1-C4 alkyl, C1-C4 haloalkyl, CN, halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, or C1-C4 haloalkylsulfonyl;
R5 and R8 are each independently H; C1-C4 alkyl; halogen; R12; G; O-G; S(O)p-G; S(O)p-phenyl optionally substituted with one to three substituents independently selected from W and optionally substituted with one R12; C1-C10 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy or C1-C4 alkythio, each substituted with one or more substituents selected from the group consisting of G, R6, halogen, CN, NO2, NH2, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C3-C6 trialkylsilyl, a phenyl ring and a phenoxy ring, each phenyl and phenoxy ring optionally substituted with from one to three substituents independently selected from W and optionally substituted with one R12;
each G is independently C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C3-C7 cyanocycloalkyl, C4-C7 alkylcycloalkyl, C4-C8 cycloalkylalkyl, or C4-C8 halocycloalkylalkyl;
each R6 is independently R13C(=E)-; R14C(=E)L-; R13LC(=E)-; (R14)LC(=E)L-; —O(Q=)P(OR14)2; —SO2LR13; or R14SO2L-;
each E is independently O, S, NR15, NOR15, NN(R15)2, N—S═O, N—CN or N—NO2;
R7 is H, C1-C4 alkyl, C1-C4 haloalkyl, halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, or C1-C4 haloalkylsulfonyl;
R9 is CF3, OCF3, OCHF2, OCH2CF3, S(O)pCF3, S(O)pCHF2 or halogen;
R10 is H, C1-C4 alkyl, C1-C4 haloalkyl, halogen, CN or C1-C4 haloalkoxy;
each R11 is independently C1-C6 alkylthio; C1-C6 haloalkythio; phenylthio; SN(R16)2; R13C(═O)—; R14C(═O)L-; R13LC(═O)—; or R13LC(═O)NR13S—;
each L is independently O, NR13 or S;
each R12 is independently B(OR17)2; NH2; SH; thiocyanato; C3-C8 trialkylsilyloxy; C1-C4 alkyldisulfide; SF5; R13C(=E)-; R14C(=E)L-; R13LC(=E)-; (R13)LC(=E)L-; —OP(=Q)(OR14)2; —SO2LR13; or R14SO2L-;
Q is O or S;
each R13 is independently hydrogen; C1-C6 alkyl, or C1-C6 haloalkyl;
each R14 is C1-C6 alkyl, C1-C6 haloalkyl or phenyl optionally substituted with from one to three substituents independently selected from W and optionally substituted with R12;
each R15 is independently H; C1-C6 haloalkyl; C1-C4 alkyl optionally substituted with one or more substituents selected from the group consisting of CN, NO2, R6, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C3-C6 trialkylsilyl, and a phenyl ring optionally substituted with one to three substituents independently selected from W and optionally substituted with one R12; or phenyl optionally substituted with one to three substituents independently selected from W and optionally substituted with R12;
each R17 is independently H or C1-C4 alkyl;
each W is independently C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C4-C6(alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; and
each p is independently 0, 1 or 2;
provided that when both (a) R5 is H, C1-C4 alkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C1-C4 haloalkoxy, C1-C4 haloalkylthio, halogen, C3-C6 cycloalkyl, C3-C6 halocycloalkyl or optionally substituted benzyl; and (b) R8 is H, C1-C4 alkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C1-C4 haloalkoxy, C1-C4 haloalkylthio, halogen, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl or C3-C8 dialkylaminocarbonyl; then both (c) at least one substituent selected from the group consisting of R6, R11 and R12 is present; and (d) at least one R6 is other than C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl or C3-C8 dialkylaminocarbonyl; and/or at least one R11 is other than C1-C4 alkylthio, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl or C3-C8 dialkylaminocarbonyl; and/or at least one R12, if present, is other than C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylamioncarbonyl or C3-C8 dialkylaminocarbonyl.