Substituted cyclic amides and their use as herbicides

A compound of from Formula 1, an N-oxide of the compound, or a salt of the compound or N-oxide:

• wherein
• Q1 is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7;
• or a 4- to 7-membered heterocyclic ring or an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 5 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members;
• or
• Q1 is C2-C10 alkenyl, C2-C10 alkynyl, C2-C10 haloalkenyl, C2-C10 haloalkynyl, C4-C10 cycloalkenyl, C4-C10 halocycloalkenyl, C2-C8 alkylcarbonyl or C2-C8 alkoxyalkyl;
• Q2 is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R10;
• or a 4- to 7-membered heterocyclic ring or an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)(═NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R10 on carbon atom ring members and selected from R11 on nitrogen atom ring members;
• or
• Q2 is C2-C10 alkenyl, C2-C10 alkynyl, C2-C10 haloalkenyl, C2-C10 haloalkynyl, C4-C10 cycloalkenyl, C4-C10 halocycloalkenyl, C2-C8 alkylcarbonyl or C2-C8 alkoxyalkyl;
• J is —CR2R3—, —NR2a— or —O—;
• Y1 and Y2 are each independently O, S or NR12;
• R1 is H, hydroxy, amino, cyano, formyl, C3-C8 alkylcarbonylalkyl, —C(C1-C4 alkyl)=N—O(C1-C4 alkyl), —C(O)NH2, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C6 cyanoalkyl, C3-C6 cycloalkyl, C4-C8 cycloalkenyl, C4-C8 cycloalkylalkyl, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 haloalkenylalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C5-C10 cycloalkylcarbonylalkyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl;
• or —CPh=N—O(C1-C4 alkyl), each optionally substituted on ring members with up to 5 substituents independently selected from R13;
• or G1;
• or W1G1;
• R2 and R3 are each independently H, halogen, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkoxy;
• or
• R2 and R3 are taken together with the carbon atom to which they are bonded to form a C3-C7 cycloalkyl ring;
• R2a is C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl or C1-C6 alkoxy;
• or
• R1 and R2a are taken together as C3-C6 alkylene or —CH2OCH2—;
• R4 and R5 are each independently H, halogen, hydroxy, C1-C4 alkoxy, C1-C4 haloalkyl or C1-C4 alkyl;
• R6 is H, hydroxy, amino, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl or C3-C10 trialkylsilyl or G1;
• or
• R6 and Q2 are taken together with the nitrogen atom to which they are both bonded to form an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members;
• each R7 and R10 is independently hydroxy, amino, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 haloalkoxyhaloalkoxy, C3-C6 cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl, 2-methylcyclopropyl, C2-C8 alkylamino, C2-C8 dialkylamino, C2-C8 halodialkylamino or C3-C8 cycloalkylamino;
• or G2;
• or
• each R7 is independently R26S(═O)═N—, R26S(═O)2NR25—C(═O)—, R26(R25N═)qS(═O)p—, wherein the free bond projecting to the right indicates the connecting point to Q1;
• or
• each R10 is independently R17ON=CR17a—, (R18)2C═NO—, (R19)2NN═CR17a—(R18)2C═NNR20a—, R20N=CR17a—, (R18)2C═N—, R17ON=CR17aC(R23b)2—, (R18)2C═NOC(R24a)2—, R26S(═O)═N—, R26S(═O)2NR25—C(═O)— or R26(R25N═)qS(═O)p—, wherein the free bond projecting to the right indicates the connecting point to Q2;
• each R8 is independently H, cyano, C2-C3 alkylcarbonyl or C2-C3 haloalkylcarbonyl;
• each R9 and R11 is independently cyano, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C6 cycloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl, C2-C3 alkylaminoalkyl or C3-C4 dialkylaminoalkyl;
• each R12 is independently H, cyano, hydroxy, CHO, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, —(C═O)CH3 or —(C═O)CF3;
• each G1 is independently phenyl, or a 5- or 6-membered heterocyclic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R13;
• each G2 is a 5- or 6-membered heterocyclic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R14;
• W1 is C1-C3 alkylene, C2-C4 alkenylene, C2-C4 alkynylene, —(C1-C2 alkylene)C(═O)—, —C(═O)(C1-C2 alkylene)-, —CH2O—, —CH2NH—, —OCH2—, —NCH2—, —N—, —O—, —S—, —SO— or —SO2— wherein the free bond projecting to the left indicates the connecting point of W1 to N and the free bond projecting to the right indicates the connecting point of W1 to G1;
• each R13 and R14 is independently halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH2, —SO2NH2, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C2-C8 alkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl, C1-C6 alkylamino, C2-C8 dialkylamino, C2-C8 alkylcarbonylamino, C1-C6 alkylsulfonylamino, phenyl, pyridinyl or thienyl;
• each R17 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
• each R17a is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C3-C10 trialkylsilyl or G1;
• each R18 is independently H, hydroxy, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
• each R19 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
• each R20 is independently H, hydroxy, amino, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
• each R20a is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C3-C10 trialkylsilyl or G1;
• each R23b is independently H, halogen, cyano, hydroxy, C1-C4 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl or C3-C6 cycloalkyl;
• each R24a is independently H, C1-C4 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl or C3-C6 cycloalkyl;
• each R25 is independently H, cyano, C2-C3 alkylcarbonyl or C2-C3 haloalkylcarbonyl;
• each R26 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C3-C10 trialkylsilyl or G1;
• and
• each u and v are independently 0, 1 or 2 in each instance of S(═O)u(═NR8)v, provided that the sum of u and v is 0, 1 or 2;
• each p and q are independently 0, 1 or 2 in each instance of R26(R25N═)qS(═O)p—, provided that the sum of u and v is 0, 1 or 2 and when p is 0, q is other than 1 or 2.