Arthropodicidal 1,2,4-triazinyl amides

A compound of the formula ##STR40## wherein Q is ##STR41## A is H;

• E is selected from the group H and C.sub.1 -C.sub.3 alkyl;
• or
• A and E are 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 ##STR42## X is selected from the group O and S;
• Y is selected from the group H;
• C.sub.1 -C.sub.6 alkyl;
• benzyl;
• C.sub.2 -C.sub.6 alkenyl;
• C.sub.2 -C.sub.6 alkynyl;
• C.sub.1 -C.sub.6 alkyl substituted by halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, S(O).sub.r R.sup.30, P(X) (OR.sup.25).sub.2, C(O)R.sup.30, C(O).sub.2 R.sup.30 and phenyl optionally substituted by 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 halocycloalkyl;
• C.sub.4 -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;
• C(O)R.sup.33 ;
• C(O).sub.2 R.sup.33 ;
• C(S)R.sup.26 ;
• C(S)R.sup.33 ;
• C(O)C(O).sub.2 R.sup.25 ;
• C(O)CH.sub.2 C(O).sub.2 R.sup.25 ;
• S(O).sub.r R.sup.30 ;
• S(O).sub.2 CH.sub.2 C(O).sub.2 R.sup.25 ;
• P(X) (OR.sup.25).sub.2 ;
• phenylthio;
• R.sup.11 OC(O)N(R.sup.12)S--;
• R.sup.13 (R.sup.14)NS--;
• N.dbd.CR.sup.9 R.sup.10 ;
• OR.sup.8 ;
• NR.sub.8 R.sup.9 ;
• and R.sup.38 ;
• Y being other than N.dbd.CR.sup.9 R.sup.10, OR.sup.8, and NR.sup.8 R.sup.9 when Q is Q-8 and A and E are taken together as --CH.sub.2 --;
• 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.16, SR.sup.16, S(O)R.sup.16, S(O).sub.2 R.sup.16, OC(O)R.sup.16, OS(O).sub.2 R.sup.16, C(O)R.sup.16, C(O).sub.2 R.sup.16, C(O)NR.sup.16 R.sup.17, S(O).sub.2 NR.sup.16 R.sup.17, NR.sup.16 R.sup.17, NR.sup.17 C(O)R.sup.16, OC(O)NHR.sup.16, NR.sup.17 C(O)NHR.sup.16, NR.sup.17 S(O).sub.2 R.sup.16, 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 are taken together, or (R.sup.2).sub.2 are 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.16, S(O).sub.2 R.sup.16, OC(O)R.sup.16, NR.sup.17 S(O).sub.2 R.sup.16 or OS(O).sub.2 R.sup.16 then R.sup.16 is other than H;
• R.sup.3 is selected from the group H, J, N.sub.3, NO.sub.2, halogen, N(R.sup.21)R.sup.22, C(R.sup.31).dbd.N--O--R.sup.32, 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 alkoxyalkyl, C.sub.3 -C.sub.8 alkoxycarbonyl-alkyl, C(O)R.sup.16, C(O).sub.2 R.sup.16, OR.sup.18, C(O)NR.sup.16 R.sup.17, C(S)NR.sup.16 R.sup.17, C(S)R.sup.16, C(S)SR.sup.16, CN, Si(R.sup.25) (R.sup.26) (R.sup.27), SR.sup.25, S(O)R.sup.25, S(O).sub.2 R.sup.25, P(O) (OR.sup.25).sub.2, phenyl optionally substituted with (R.sup.15).sub.p, and benzyl optionally 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 one or more members independently selected from the group C.sub.1 -C.sub.3 alkyl, CN, C(O)R.sup.23, C(O).sub.2 R.sup.23, and phenyl optionally substituted with W;
• or R.sup.3 is C.sub.1 -C.sub.6 alkyl substituted with one or more members independently selected from the group C(O)N(R.sup.24)R.sup.34, C(O)R.sup.24, SR.sup.25, S(O)R.sup.25, S(O).sub.2 R.sup.25, SCN, CN, C.sub.1 -C.sub.2 haloalkoxy, Si(R.sup.25) (R.sup.26) (R.sup.27), N(R.sup.21)R.sup.22, NO.sub.2, OC(O)R.sup.24, P(O) (OR.sup.25).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, 0-2 sulfur and 0-4 nitrogen, this substituent optionally containing one carbonyl and optionally substituted with one or more members independently selected from W;
• R.sup.4 and R.sup.5 are independently selected from the group H, C.sub.1 -C.sub.4 alkyl, C(O)R.sup.19 and C.sub.2 -C.sub.4 alkoxycarbonyl;
• 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.16, S(O)R.sup.16, S(O).sub.2 R.sup.16, C(O)R.sup.16, C(O).sub.2 R.sup.16, C(O)NR.sup.16 R.sup.20, C(S)NR.sup.16 R.sup.20, C(S)R.sup.16, C(S)OR.sup.16, P(O) (OR.sup.16).sub.2, P(S) (OR.sup.16).sub.2, P(O) (R.sup.16)OR.sup.16, P(O) (R.sup.16)SR.sup.20, optionally substituted phenyl, and optionally substituted benzyl wherein the optional phenyl and benzyl substituents are independently 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.16, C(O)NR.sup.16 R.sup.20 or C(S)NR.sup.16 R.sup.20 then R.sup.16 is other than H;
• R.sup.8 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 alkynyl, S(O).sub.2 NR.sup.17 R.sup.18, S(O).sub.2 R.sup.16, C(O)R.sup.16, C(O).sub.2 R.sup.16, C(O)NR.sup.16 R.sup.20, phenyl optionally substituted with halogen or C.sub.1 -C.sub.4 alkoxy, and benzyl optionally substituted with halogen;
• provided that when R.sup.8 is S(O).sub.2 R.sup.16 R.sup.16 is other than H;
• R.sup.9 is selected from the group H, C.sub.1 -C.sub.4 alkyl and C(O)R.sup.16 ;
• R.sup.10 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl and phenyl optionally substituted with one or more members independently selected from the group halogen, CN, NO.sub.2, CF.sub.3 and OCF.sub.3 ;
• or
• R.sup.9 and R.sup.10 are taken together as --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --;
• R.sup.11 is C.sub.1 -C.sub.18 alkyl;
• R.sup.12 is C.sub.1 -C.sub.4 alkyl;
• R.sup.13 and R.sup.14 are independently C.sub.1 -C.sub.4 alkyl;
• or
• R.sup.13 and R.sup.14 are 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.15 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.16, SR.sup.16, S(O)R.sup.16, S(O).sub.2 R.sup.16, OC(O)R.sup.16, OS(O).sub.2 R.sup.16, C(O)R.sup.16, C(O).sub.2 R.sup.16, C(O)NR.sup.16 R.sup.17, S(O).sub.2 NR.sup.16 R.sup.17, NR.sup.16 R.sup.17, NR.sup.17 C(O)R.sup.16, OC(O)NHR.sup.16, NR.sup.17 C(O)NHR.sup.16, NR.sup.17 S(O).sub.2 R.sup.16, 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.15).sub.2 are 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.15 is S(O)R.sup.16, S(O).sub.2 R.sup.16, OC(O)R.sup.16, NR.sup.17 S(O).sub.2 R.sup.16 or OS(O).sub.2 R.sup.16 then R.sup.16 is other than H;
• R.sup.16 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 optionally substituted benzyl wherein the optional phenyl and benzyl substituents are 1 to 3 substituents independently selected from W;
• R.sup.17 is selected from the group H and C.sub.1 -C.sub.4 alkyl;
• or
• R.sup.16 and R.sup.17, when attached to the same atom, are 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.18 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 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.21 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, all of these optional substituents being independently selected from C.sub.1 -C.sub.2 alkoxy, CN, C(O)R.sup.28 or C(O).sub.2 R.sup.25 ;
• R.sup.22 is selected from the group H, C.sub.1 -C.sub.3 alkyl, phenyl optionally substituted with at least one member independently selected from W, and benzyl optionally substituted with at least one member independently selected from W;
• R.sup.23 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.24 is selected from the group H and C.sub.1 -C.sub.3 alkyl;
• R.sup.25 is selected from the group C.sub.1 -C.sub.3 alkyl and phenyl optionally substituted with at least one member independently selected from W;
• R.sup.26 is selected from the group C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, and C.sub.1 -C.sub.4 haloalkoxy;
• R.sup.27 is C.sub.1 -C.sub.3 alkyl;
• R.sup.28 is selected from the group H, C.sub.1 -C.sub.3 alkyl and phenyl optionally substituted with at least one member independently selected from W;
• R.sup.30 is selected from the group C.sub.1 -C.sub.3 alkyl and C.sub.1 -C.sub.3 haloalkyl;
• R.sup.31 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 alkylthio and CN;
• R.sup.32 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.33 is selected from the group C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, and phenyl optionally substituted with at least one member independently selected from W;
• R.sup.34 is selected from the group H and C.sub.1 -C.sub.2 alkyl;
• R.sup.35 is selected from the group CHO, C.sub.1 -C.sub.4 alkyl substituted with substituents independently selected from the group halogen, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 alkoxycarbonyl and N(R.sup.36) (R.sup.37);
• or
• R.sup.35 is C.sub.2 -C.sub.6 haloalkylcarbonyl;
• C.sub.3 -C.sub.6 alkenyl;
• C.sub.3 -C.sub.6 haloalkenyl;
• C.sub.3 -C.sub.6 alkynyl;
• C.sub.3 -C.sub.6 haloalkynyl;
• C.sub.3 -C.sub.6 cycloalkyl;
• C(S)R.sup.26 ;
• C(S)R.sup.33 ;
• C(O)C(O).sub.2 R.sup.25 ;
• C(O)CH.sub.2 C(O).sub.2 R.sup.25 ;
• S(O).sub.r R.sup.30 ;
• S(O).sub.2 CH.sub.2 C(O).sub.2 R.sup.25 ;
• P(X) (OR.sup.25).sub.2 ;
• C(O)N(R.sup.36) (R.sup.37);
• S(O).sub.r N(R.sup.13)R.sup.14 ;
• S(O).sub.r N(R.sup.12)C(O)OR.sup.11 ;
• S(O).sub.r N(R.sup.12)CHO;
• J;
• CH.sub.2 J;
• C(O)J;
• C(O)Ph where the phenyl group is optionally substituted by a group independently selected from W;
• and benzyl optionally substituted by a group independently selected from W;
• R.sup.36 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkenyl, phenyl optionally substituted by a group independently selected from W and benzyl optionally substituted by a group independently selected from W;
• R.sup.37 is selected from the group C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 alkenyl;
• R.sup.38 is selected from the group C(S)R.sup.26, C(S)R.sup.33, C(O)C(O)2R.sup.25, C(O)CH.sub.2 C(O).sub.2 R.sup.25, S(O)R.sup.30, S(O).sub.2 R.sup.30, S(O).sub.2 CH.sub.2 C(O).sub.2 R.sup.25, P(X) (OR.sup.25).sub.2, C.sub.3 -C.sub.6 haloalkynyl, and C.sub.1 -C.sub.6 alkyl substituted by P(X) (OR.sup.25).sub.2 ;
• 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;
• and
• r is 0, 1 or 2.