Arthropodicidal carboxanilides

A compound of Formula I or II:

• ##STR117## wherein:
• Q is selected from the group ##STR118## A is H;
• E is selected from the group H and C.sub.1 -C.sub.3 alkyl;
• or
• A and E can be taken together to form --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --O--, --S--, --S(O)--, --S(O).sub.2 --, --NR.sup.7 --, --OCH.sub.2 --, --SCH.sub.2 --, --N(R.sup.7)CH.sub.2 --, substituted --CH.sub.2 --, and substituted --CH.sub.2 CH.sub.2 -- the substituents independently selected from 1-2 halogen and 1-2 methyl;
• G is selected from the group ##STR119## X is selected from the group O, S and N-X.sup.2 ;
• X.sup.1 is selected from the group Cl, Br, OR.sup.8, SR.sup.8 and NR.sup.8 R.sup.9 ;
• X.sup.2 is selected from the group R.sup.8, OH, OR.sup.8, CN, SO.sub.2 R.sup.8, SO.sub.2 Ph, OC(O)NR.sup.9 R.sup.10, OC(O)OR.sup.8, NR.sup.9 R.sup.10 and phenyl optionally substituted with R.sup.11 ;
• Y is selected from the group H;
• C.sub.1 -C.sub.6 alkyl;
• benzyl;
• C.sub.2 -C.sub.6 alkoxyalkyl;
• C.sub.2 -C.sub.6 alkenyl;
• C.sub.2 -C.sub.6 alkynyl;
• C.sub.1 -C.sub.6 alkyl optionally substituted with halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, CN, NO.sub.2, S(O).sub.r R.sup.32, COR.sup.32, CO.sub.2 R.sup.32, phenyl optionally substituted with halogen, CN, C.sub.1 -C.sub.2 haloalkyl and C.sub.1 -C.sub.2 haloalkoxy;
• C.sub.3 -C.sub.6 cycloalkyl;
• C.sub.3 -C.sub.6 cyclohaloalkyl;
• C.sub.3 -C.sub.6 cycloalkylalkyl;
• CHO;
• C.sub.2 -C.sub.6 alkylcarbonyl;
• C.sub.2 -C.sub.6 alkoxycarbonyl;
• C.sub.2 -C.sub.6 haloalkylcarbonyl;
• COR.sup.36 ;
• CO.sub.2 R.sup.36 ;
• C.sub.1 -C.sub.6 alkylthio;
• C.sub.1 -C.sub.6 haloalkylthio;
• phenylthio;
• R.sup.12 OC(O)N(R.sup.13)S-- and R.sup.14 (R.sup.15)NS--;
• A.sup.1 is H;
• A.sup.1 and Y can be taken together to form --(CH.sub.2).sub.t --;
• Z is C or N;
• Z.sup.1 is NR.sup.31 ;
• R.sup.1 and R.sup.2 are independently selected from the group H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, halogen, CN, N.sub.3, SCN, NO.sub.2, OR.sup.17, SR.sup.17, S(O)R.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17, OS(O).sub.2 R.sup.17, CO.sub.2 R.sup.17, C(O)R.sup.17, C(O)NR.sup.17 R.sup.18, SO.sub.2 NR.sup.17 R.sup.18, NR.sup.17 R.sup.18, NR.sup.18 C(O)R.sup.17, OC(O)NHR.sup.17, NR.sup.18 C(O)NHR.sup.17, NR.sup.18 SO.sub.2 R.sup.17, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W;
• or when m or n is 2, (R.sup.1).sub.2 can be taken together, or (R.sup.2).sub.2 can be taken together as --OCH.sub.2 O--, --OCF.sub.2 O--, --OCH.sub.2 CH.sub.2 O--, --CH.sub.2 C(CH.sub.3).sub.2 O--, --CF.sub.2 CF.sub.2 O or --OCF.sub.2 CF.sub.2 O-- to form a cyclic bridge;
• provided that when R.sup.1 or R.sup.2 is S(O)R.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17 or OS(O).sub.2 R.sup.17 then R.sup.17 is other than H;
• R.sup.3 is selected from the group H, J, N.sub.3, NO.sub.2, halogen, N(R.sup.22)R.sup.23, C(R.sup.34).dbd.N--O--R.sup.35, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.2 -C.sub.6 alkoxylalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, CO.sub.2 R.sup.17, OR.sup.19, C(O)R.sup.17, C(O)NR.sup.17 R.sup.18, C(S)NR.sup.17 R.sup.18, C(S)R.sup.17, C(S)SR.sup.17, CN, Si(R.sup.28) (R.sup.29)R.sup.27, SR.sup.27, S(O)R.sup.27, SO.sub.2 R.sup.27, --P(O) (OR.sup.27).sub.2, phenyl, phenyl substituted with (R.sup.16).sub.p, benzyl and benzyl substituted with 1 to 3 substituents independently selected from W;
• or R.sup.3 is C.sub.2 -C.sub.6 epoxyalkyl optionally substituted with a group selected from C.sub.1 -C.sub.3 alkyl, CN, C(O)R.sup.24, CO.sub.2 R.sup.24 and phenyl optionally substituted with W;
• or R.sup.3 is C.sub.1 -C.sub.6 alkyl substituted with a group selected from C(O)N(R.sup.25)R.sup.26, C(O)R.sup.25, SR.sup.27, S(O)R.sup.27, SO.sub.2 R.sup.27, SCN, CN, C.sub.1 -C.sub.2 haloalkoxy, Si(R.sup.28) (R.sup.29)R.sup.30, N(R.sup.22)R.sup.23, NO.sub.2, OC(O)R.sup.25, --P(O) (OR.sup.27).sub.2 and J;
• J is selected from the group saturated, partially unsaturated or aromatic 5- or 6-membered heterocyclic ring, bonded through carbon or nitrogen, containing 1-4 heteroatoms independently selected from the group consisting of 0-2 oxygen, 0-3 sulfur and 0-4 nitrogen, this substituents optionally containing one carbonyl and optionally substituted with one or more members selected from W;
• R.sup.4 and R.sup.5 are independently selected from the group H, C.sub.1 -C.sub.4 alkyl, COR.sup.20 and C.sub.2 -C.sub.4 alkoxycarbonyl;
• or
• R.sup.4 and R.sup.5 can be taken together to form .dbd.O or .dbd.S;
• R.sup.6 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 haloalkoxycarbonyl, C.sub.2 -C.sub.4 alkoxycarbonyl C.sub.2 -C.sub.4 haloalkoxycarbonyl, COR.sup.36, CO.sub.2 R.sup.36, C.sub.2 -C.sub.5 alkylaminocarbonyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, C.sub.4 -C.sub.7 alkylcycloalkyl, C.sub.4 -C.sub.7 haloalkylcycloalkyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfonyl and SO.sub.2 Ph optionally substituted with Cl, Br or CH.sub.3 ;
• R.sup.7 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 haloalkenyl, SR.sup.17, S(O)R.sup.17, S(O).sub.2 R.sup.17, R.sup.17, CO.sub.2 R.sup.17, C(O)NR.sup.17 R.sup.21, C(S)NR.sup.17 R.sup.21, C(S)R.sup.17, C(S)OR.sup.17, --P(O)(OR.sup.17).sub.2, --P(S)(OR.sup.17).sub.2, P(O)(R.sup.17)OR.sup.17, P(O)(R.sup.17)SR.sup.21, and optionally substituted phenyl and benzyl wherein the substituent(s) are selected from F, Cl, Br, CH.sub.3, CF.sub.3 or OCF.sub.3 ;
• provided that when R.sup.7 is other than C(O)R.sup.17, C(O)NR.sup.17 R.sup.21 or C(S)NR.sup.17 R.sup.21 then R.sup.17 is other than H;
• R.sup.8 is selected from the group C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.6 cycloalkyl;
• C.sub.1 -C.sub.3 alkyl substituted with OCH.sub.3, OCH.sub.2 CH.sub.3, NO.sub.2, CN, CO.sub.2 CH.sub.3, CO.sub.2 CH.sub.2 CH.sub.3, SCH.sub.3 or SCH.sub.2 CH.sub.3 and benzyl optionally substituted with R.sup.11 ;
• R.sup.9 is selected from the group H, C.sub.1 -C.sub.4 alkyl C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkoxycarbonyl, and optionally substituted phenyl and pyridine wherein the substituent(s) are selected from R.sup.15 ;
• or
• R.sup.8 and R.sup.9 can be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 -- each of which is optionally and independently substituted with 1 or 2 CH.sub.3 groups;
• R.sup.10 is selected from the group H and C.sub.1 -C.sub.4 alkyl;
• or
• R.sup.9 and R.sup.10 can be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 -- each of which is optionally and independently substituted with 1 or 2 CH.sub.3 groups;
• R.sup.11 is selected from halogen, CN, C.sub.1 -C.sub.3 haloalkyl and C.sub.1 -C.sub.3 haloalkoxy;
• R.sup.12 is C.sub.1 -C.sub.6 alkyl;
• R.sup.13 is C.sub.1 -C.sub.4 alkyl;
• R.sup.14 and R.sup.15 are independently C.sub.1 -C.sub.4 alkyl;
• or
• R.sup.14 and R.sup.15 can be taken together as --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
• R.sup.16 is selected from the group C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, halogen, CN, N.sub.3, SCN, NO.sub.2, OR.sup.17, SR.sup.17, S(O)R.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17, OS(O).sub.2 R.sup.17, CO.sub.2 R.sup.17, C(O)R.sup.17, C(O)NR.sup.17 R.sup.18, SO.sub.2 NR.sup.17 R.sup.18, NR.sup.17 R.sup.18, NR.sup.18 C(O)R.sup.17, OC(O)NHR.sup.17, NR.sup.18 C(O)NHR.sup.17, NR.sup.18 SO.sub.2 R.sup.17, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W;
• or when p is 2, (R.sup.16).sub.2 can be taken together as --OCH.sub.2 O--, --OCF.sub.2 O--, --OCH.sub.2 CH.sub.2 O--, --CH.sub.2 C(CH.sub.3).sub.2 O--, --CF.sub.2 CF.sub.2 O or --OCF.sub.2 CF.sub.2 O-- to form a cyclic bridge;
• provided that when R.sup.16 is S(O)R.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17 or OS(O).sub.2 R.sup.17 then R.sup.17 is other than H;
• R.sup.17 is selected from the group H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, and optionally substituted phenyl and benzyl wherein the substituents are 1 to 3 substituents independently selected from W;
• R.sup.18 is selected from the group H and C.sub.1 -C.sub.4 alkyl;
• or
• R.sup.17 and R.sup.18, when attached to the same atom, can be taken together as --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
• R.sup.19 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 alkoxycarbonyl and C.sub.1 -C.sub.4 alkylsulfonyl;
• R.sup.20 is C.sub.1 -C.sub.3 alkyl;
• R.sup.21 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl and C.sub.2 -C.sub.4 alkynyl;
• R.sup.22 is selected from the group H, C.sub.2 -C.sub.7 alkylcarbonyl, C.sub.2 -C.sub.7 alkoxycarbonyl, optionally substituted C.sub.1 -C.sub.4 alkyl, optionally substituted C.sub.2 -C.sub.4 alkenyl, and optionally substituted C.sub.2 -C.sub.4 alkynyl, the substituents selected from C.sub.1 -C.sub.2 alkoxy, CN, C(O)R.sup.30 and C(O).sub.2 R.sup.27 ;
• R.sup.23 is selected from the group H, C.sub.1 -C.sub.3 alkyl, phenyl, phenyl substituted with W, benzyl and benzyl substituted with W;
• R.sup.24 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl and C.sub.2 -C.sub.4 alkynyl;
• R.sup.25 and R.sup.26 are independently selected from the group H and C.sub.1 -C.sub.2 alkyl;
• R.sup.27 is selected from the group C.sub.1 -C.sub.3 alkyl, phenyl and phenyl substituted with W;
• R.sup.28 is C.sub.1 -C.sub.3 alkyl;
• R.sup.29 is C.sub.1 -C.sub.3 alkyl;
• R.sup.30 is selected from the group H, C.sub.1 -C.sub.3 alkyl, phenyl and phenyl substituted with W;
• R.sup.31 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkylcarbonyl or C.sub.2 -C.sub.4 alkoxycarbonyl;
• R.sup.32 is selected from the group C.sub.1 -C.sub.3 alkyl;
• R.sup.34 is selected from the group H, Cl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.2 thioalkyl and CN;
• R.sup.35 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 alkylcarbonyl and C.sub.2 -C.sub.3 alkoxycarbonyl;
• R.sup.36 is selected from the group phenyl and phenyl substituted with W;
• W is selected from the group halogen, CN, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio, C.sub.1 -C.sub.2 alkylsulfonyl and C.sub.1 -C.sub.2 haloalkylsulfonyl;
• m is 1 to 3;
• n is 1 to 3;
• p is 1 to 3;
• r is 0, 1 or 2;
• t is 2 or 3;
• and
• u is 1 or 2.