Pyridazinones as herbicides

1. A compound selected from Formula 1, N-oxides and salts thereof

wherein

A is phenyl substituted with R 3 ; or a 5- or 6-membered heteroaromatic ring, said ring substituted with R 4 on carbon ring members and with R 5 on nitrogen ring members and attached to the remainder of Formula 1 through a carbon atom;

R 1 is H, halogen, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkoxyalkyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 2 -C 6 alkylcarbonyloxy, C 1 -C 4 hydroxyalkyl, SO p (R 16 ), C 2 -C 4 alkylthioalkyl, C 2 -C 4 alkylsulfonylalkyl, C 1 -C 4 alkylamino, C 2 -C 4 dialkylamino, C 3 -C 6 cycloalkyl or hydroxy;

R 2 is H, halogen, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkoxyalkyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 2 -C 6 alkylcarbonyloxy, C 1 -C 4 hydroxyalkyl, SO q (R 17 ), C 2 -C 4 alkylthioalkyl, C 2 -C 4 alkylsulfonylalkyl, C 1 -C 4 alkylamino, C 2 -C 4 dialkylamino, C 3 -C 6 cycloalkyl or hydroxy; or

R 1 and R 2 are taken together as C 3 -C 6 alkylene or C 3 -C 6 alkenylene;

Q is C(R 6 )(R 7 ) or O;

J is phenyl substituted with 1 R 9 and optionally substituted with up to 2 R 10 ; or

J is a 6-membered heteroaromatic ring substituted with 1 R 9 and optionally substituted with up to 2 R 10 on carbon ring members; or

J is a 5-membered heteroaromatic ring substituted with 1 R 11 on carbon ring members and R 13 on nitrogen ring members; and optionally substituted with 1 R 12 on carbon ring members;

each R 3 is independently H, halogen, cyano, nitro, SF 5 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy or S(O) r R 18 ;

each R 4 is independently H, halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or S(O) t R 19 ;

R 5 is H, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 6 is H, F, Cl, Br, cyano, C 1 -C 4 alkyl, OH, C 1 -C 4 haloalkyl, OR 14a or CO 2 R 15a ;

R 7 is H, F, Cl, Br, cyano, C 1 -C 4 alkyl, OH, C 1 -C 4 haloalkyl, OR 14b or CO 2 R 15b ; or

R 6 and R 7 are taken together with the carbon to which they both are attached to form C(═O), C(═NOR 24 ) or C(═N—N(R 25 )(R 26 ));

R 9 is SF 5 , C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or S(O) u R 20 ;

each R 10 is independently halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or S(O) v R 21 ; or

R 9 and R 10 are taken together with two adjacent carbon atoms to form a 5-membered ring containing ring members selected from carbon atoms and up to two O atoms and up to two S atoms, and optionally substituted on carbon atom ring members with up to five halogen atoms;

R 11 is SF 5 , C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or S(O) w R 22 ;

R 12 is halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or S(O) x R 23 ;

R 13 is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

each R 14a and R 14b is independently C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; or

R 14a and R 14b are taken together as —CH 2 CH 2 — or —CH 2 CH 2 CH 2 —;

each R 15a and R 15b is independently C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

each R 16 , R 17 , R 18 , R 19 , R 20 , R 22 and R 23 is independently C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 21 is C 1 -C 4 haloalkyl;

R 24 is H or C 1 -C 4 alkyl;

R 25 is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 26 is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; and

each p, q, r, t, u, v, w and x is independently 0, 1 or 2.

2. The compound of claim 1 wherein

A is phenyl substituted with R 3 ; or a 6-membered heteroaromatic ring, said ring substituted with R 4 on carbon ring members and with R 5 on nitrogen ring members and attached to the remainder of Formula 1 through a carbon atom;

R 1 is H, halogen, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkoxyalkyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl or C 2 -C 4 alkynyl;

R 2 is H, halogen, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkoxyalkyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 2 -C 6 alkylcarbonyloxy, C 1 -C 4 hydroxyalkyl, SO q (R 17 ), C 2 -C 4 alkylthioalkyl, C 2 -C 4 alkylsulfonylalkyl, C 1 -C 4 alkylamino, C 2 -C 4 dialkylamino or C 3 -C 6 cycloalkyl; or

R 1 and R 2 are taken together as C 3 -C 6 alkylene;

J is independently selected from J-1 through J-33;

each R 3 is independently H, halogen, cyano, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

each R 4 is independently H, halogen, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy;

R 5 is H, halogen or C 1 -C 4 haloalkyl;

R 6 is H, Cl or C 1 -C 4 alkyl;

R 7 is H, F, Cl, OH, C 1 -C 4 haloalkyl, OR 14b or CO 2 R 15b ; or

R 6 and R 7 are taken together with the carbon to which they both are attached to form C(═O);

R 9 is C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or S(O) u R 20 ;

each R 10 is independently halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; or

R 9 and R 10 are taken together with two adjacent carbon atoms to form a 5-membered ring containing ring members selected from carbon atoms and two O atoms, and optionally substituted on carbon atom ring members with up to 2 halogen atoms;

R 11 is C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or S(O) w R 22 ;

R 12 is halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 13 is H, CH 3 or CH 2 CF 3 ;

each R 14b is independently C 1 -C 4 alkyl;

each R 15b is independently C 1 -C 4 alkyl;

each R 17 , R 20 and R 22 is independently C 1 -C 4 alkyl;

R 21 is CF 3 ; and

each q, u, w and x is independently 0 or 2.

3. The compound of claim 2 wherein

A is phenyl substituted with R 3 ;

R 1 is H, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 2 is H, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 2 -C 6 alkylcarbonyloxy, C 1 -C 4 alkylamino or C 2 -C 4 dialkylamino; or

R 1 and R 2 are taken together as C 4 alkylene;

J is selected from J-1 through J-14;

each R 3 is independently H, halogen or C 1 -C 4 haloalkyl;

each R 4 is independently H, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl;

R 6 is H, Cl or CH 3 ;

R 7 is H, OH or OR 14b ;

R 9 is CF 3 , CH 2 CF 3 , —OCF 3 or —SCF 3 ; and

each R 10 is independently Cl, F or CH 3 .

4. The compound of claim 3 wherein

R 1 is H or C 1 -C 4 alkyl;

R 2 is C 1 -C 4 alkoxy, C 1 -C 4 alkyl or C 2 -C 4 dialkylamino;

Q is O;

J is selected from J-1 and J-2;

each R 3 is H, F, Cl, Br or CF 3 ;

each R 4 is independently H, F, Cl, Br, CH 3 or CF 3 ;

R 9 is CF 3 ; and

each R 10 is independently F.

5. The compound of claim 3 wherein

R 1 is H or CH 3 ;

R 2 is C 1 -C 4 alkoxy;

Q is C(R 6 )(R 7 );

R 6 is H, Cl or CH 3 ; and

R 7 is H or OH.

6. The compound of claim 2 wherein

A is phenyl substituted with R 3 ;

R 1 is H, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 2 is H, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 2 -C 6 alkylcarbonyloxy, C 1 -C 4 alkylamino or C 2 -C 4 dialkylamino; or

R 1 and R 2 are taken together as C 4 alkylene;

J is selected from J-15 through J-33;

R 6 is H, Cl or CH 3 ;

R 7 is H, OH or OR 14b ;

R 11 is CF 3 , CH 2 CF 3 , —OCF 3 or —SCF 3 ;

R 12 is Cl, CH 3 or CF 3 ;

R 13 is H or CH 3 ;

R 14b is CH 3 ; and

R 15b is CH 3 .

7. The compound of claim 2 wherein

R 1 is H or C 1 -C 4 alkyl;

R 2 is C 1 -C 4 alkoxy, C 1 -C 4 alkyl or C 2 -C 4 dialkylamino;

Q is C(R 6 )(R 7 );

J is selected from J-1 and J-2;

each R 3 is H, F, Cl, Br or CF 3 ;

each R 4 is independently H, F, Cl, Br, CH 3 or CF 3 ;

R 6 is H or CH 3 ;

R 7 is H or OH;

R 9 is CF 3 ; and

each R 10 is independently F.

8. The compound of claim 7 wherein

R 1 is H or CH 3 ;

R 2 is C 1 -C 4 alkoxy;

R 3 is H, F or CF 3 ;

R 6 is H; and

R 7 is H or OH.

9. The compound of claim 1 selected from the group consisting of

2-(4-fluorophenyl)-5-methyl-6-[[2-(trifluoromethyl)-4-pyridinyl]methyl]-3(2H)-pyridazinone;

5-methyl-2-[4-(trifluoromethyl)phenyl]-6-[[2-(trifluoromethyl)-4-pyridinyl]methyl]-3 (2H)-pyridazinone;

4-methyl-2-[4-(trifluoromethyl)phenyl]-6-[[2-(trifluoromethyl)-4-pyridinyl]oxy]-3(2H)-pyridazinone;

2-(4-fluorophenyl)-5-methyl-6-[[2-(trifluoromethyl)-4-pyridinyl]oxy]-3(2H)-pyridazinone;

5-methoxy-2-[4-(trifluoromethyl)phenyl]-6-[[2-(trifluoromethyl)-4-pyridinyl]methyl]-3(2H)-pyridazinone;

2-(4-fluorophenyl)-5-methoxy-6-[[2-(trifluoromethyl)-4-pyridinyl]methyl]-3(2H)-pyridazinone;

5-ethoxy-2-(4-fluorophenyl)-6-[hydroxy[2-(trifluoromethyl)-4-pyridinyl]methyl]-3(2H)-pyridazinone; and

5-ethoxy-2-(4-fluorophenyl)-6-[[2-(trifluoromethyl)-4-pyridinyl]methyl]-3(2H)-pyridazinone.

10. A herbicidal composition comprising a compound of claim 1 and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

11. A herbicidal composition comprising a compound of claim 1 , at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners, and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

12. A herbicidal mixture comprising (a) a compound of claim 1 , and (b) at least one additional active ingredient selected from (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) homogentisate solenesyltransererase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, and (b16) herbicide safeners; and salts of compounds of (b1) through (b16).